2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides

ABSTRACT

The invention relates to novel compounds of the formula (I)in which R1, R2, R3, R4, R5, R6, R7, R8, A1, A2, A3 and n each have the meanings given above,to their use as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for their preparation.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is the National Stage entry of InternationalApplication No. PCT/EP2017/074627, filed 28 Sep. 2017, which claimspriority to European Patent Application No. 16192636.5, filed 6 Oct.2016.

BACKGROUND Field

The present invention relates to novel 2-(het)aryl-substituted fusedbicyclic heterocycle derivatives of the formula (I), to the use thereofas acaricides and/or insecticides for controlling animal pests,particularly arthropods and especially insects and arachnids, and toprocesses and intermediates for preparation thereof.

Description of Related Art

Fused heterocycle derivatives having insecticidal properties havealready been described in the literature, for example in WO 2010/125985,WO 2012/074135, WO 2012/086848, WO 2013/018928, WO 2013/191113, WO2014/142292, WO 2014/148451, WO 2015/000715, WO 2015/121136, WO2015/133603, WO 2015/198859, WO 2015/002211, WO 2015/071180, WO2015/091945, WO 2016/005263, WO 2015/198817, WO 2016/020286, WO2016/023954, WO 2016/026848, WO2016/030229, WO 2016/039441,WO2016/039444, WO 2016/041819, WO 2016/046071, WO2016/058928,WO2016/059145, WO2016/071214, WO2016/096584, WO2016/107831,WO2016/116338, WO2016/121997, WO2016/124563, WO 2016/12457,WO2016/125621, WO2016/125622, WO 2017/025419.

However, some of the active compounds already known from the documentscited above have disadvantages in use, whether in that they have only anarrow spectrum of application or in that they do not have satisfactoryinsecticidal or acaricidal activity.

SUMMARY

Novel 2-(het)aryl-substituted fused bicyclic heterocycle derivativeshave now been found, and these have advantages over the compoundsalready known, examples of which are better biological or environmentalproperties, a wider range of application methods, better insecticidal oracaricidal activity, and also good compatibility with crop plants. The2-(het)aryl-substituted fused bicyclic heterocycle derivatives can beused in combination with further agents for improving efficacy,especially against insects that are difficult to control.

The present invention therefore provides novel compounds of the formula(I)

-   in which (configuration 1)-   A¹ represents nitrogen, ═N⁺(O⁻)— or ═C(R⁴)—,-   A² represents —N(R⁵)—, oxygen or sulfur,-   A³ represents oxygen or sulfur,-   R¹ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyl,    (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl, amino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkyl-amino, (C₃-C₈)-cycloalkylamino,    (C₁-C₆)-alkylcarbonylamino, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)alkyl,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfonylamino, aminosulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl,    di-(C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl,    -   or represents (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl,        (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, each of which is optionally        mono- or polysubstituted by identical or different substituents        from the group consisting of aryl, hetaryl and heterocyclyl,        where aryl, hetaryl or heterocyclyl may each optionally be mono-        or polysubstituted by identical or different substituents from        the group consisting of halogen, cyano, nitro, hydroxy, amino,        carboxy, carbamoyl, aminosulfonyl, (C₁-C₆)-alkyl,        (C₃-C₆)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl,        (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl,        (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylsulfimino,        (C₁-C₆)-alkylsulfimino-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulfimino-(C₂-C₆)-alkylcarbonyl,        (C₁-C₆)-alkylsulfoximino,        (C₁-C₆)-alkylsulfoximino-(C₁-C₆)-alkyl,        (C₁-C₆)-alkylsulfoximino-(C₂-C₆)-alkylcarbonyl,        (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkylcarbonyl,        (C₃-C₆)-trialkylsilyl and benzyl, or-   R¹ represents aryl, hetaryl or heterocyclyl, each of which is    optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, cyano, nitro,    hydroxy, amino, carboxyl, carbamoyl, (C₁-C₆)-alkyl,    (C₃-C₈)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl,    (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylsulfimino,    (C₁-C₆)-alkylsulfimino-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfimino-(C₂-C₆)-alkylcarbonyl,    (C₁-C₆)-alkylsulfoximino, (C₁-C₆)-alkylsulfoximino-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfoximino-(C₂-C₆)-alkylcarbonyl,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkylcarbonyl,    (C₃-C₆)-trialkylsilyl, (═O) (only in the case of heterocyclyl) and    (═O)₂ (only in the case of heterocyclyl),-   R², R³, R⁴ and R⁶ independently of one another represent hydrogen,    cyano, halogen, nitro, acetyl, hydroxy, amino, SCN,    tri-(C₁-C₆)-alkylsilyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,    (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl,    (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino,    (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,    (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,    (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,    (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,    (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,    (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylthiocarbonyl,    (C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,    (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,    (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,    (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,    (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,    (C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl    ((C₁-C₆)-alkylcarbonylamino), SF₅ or    -   represent aryl or hetaryl, each of which is optionally mono- or        polysubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, carboxyl, halogen, nitro, acetyl,        hydroxy, amino, SCN, tri-(C₁-C₆)-alkylsilyl, (C₁-C₆)-alkyl,        (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl, (C₁-C₆)-hydroxyalkyl,        hydroxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,        (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,        (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy,        (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,        (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino,        (C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,        (C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,        (C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,        (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl,        (C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,        (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,        (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,        (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,        (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,        (C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,        (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,        (C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkyl-aminocarbonyl,        (C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,        (C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,        (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,        (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,        (C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,        (C₁-C₆)-alkylaminothiocarbonyl,        di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylamino,-   R⁵ represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,    (C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,    (C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl,    (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyl,    (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,    (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,    (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,    (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl,    aminocarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylamino-(C₁-C₆)-alkyl,    di-(C₁-C₆)-alkylamino-(C₁-C₆)-alkyl or    (C₃-C₈)-cycloalkylamino-(C₁-C₆)-alkyl,-   R⁷ represents hydrogen or represents (C₁-C₆)-alkyl,    (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,    (C₃-C₆)-cycloalkyl, (C₃-C₁₂)-cycloalkyl-(C₁-C₆)-alkyl or    (C₄-C₁₂)-bicycloalkyl, each of which is optionally mono- or    polysubstituted by identical or different substituents, where the    substituents independently of one another may be selected from the    group consisting of halogen, cyano, nitro, hydroxy, (C₁-C₆)-alkyl,    (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,    (C₁-C₄)-alkylsulfonyl, (C₂-C₆)-alkoxycarbonyl,    (C₂-C₆)-alkylcarbonyl, amino, (C₁-C₄)-alkylamino,    di-(C₁-C₄-alkyl)amino, (C₃-C₆)-cycloalkylamino, a phenyl ring or a    3- or 6-membered aromatic, partially saturated or saturated    heterocycle, where the phenyl ring or heterocycle may in each case    optionally be mono- or polysubstituted by identical or different    substituents, and where the substituents independently of one    another may be selected from the group consisting of (C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,    (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,    (C₃-C₆)-halocycloalkyl, halogen, cyano, NO₂, OH, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,    (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl,    (C₁-C₄)-alkylamino, di-(C₁-C₄-alkyl)amino, (C₃-C₆)-cycloalkylamino,    (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, aminocarbonyl,    (C₁-C₆-alkyl)aminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl,-   R⁸ represents amino or (C₁-C₆)-alkylamino, di-(C₁-C₄)-alkylamino,    (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino,    (C₃-C₁₂)-cycloalkylamino, (C₃-C₁₂)-cycloalkyl-(C₁-C₆)-alkylamino,    (C₄-C₁₂)-bicycloalkylamino or hydrazino, each of which is optionally    mono- or polysubstituted by identical or different substituents,    where the substituents independently of one another may be selected    from the group consisting of halogen, cyano, amino, nitro, hydroxy,    (C═O)OH, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl,    (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylsulfonyl,    (C₁-C₄)-alkylsulfimino, (C₁-C₄)-alkylsulfoximino,    (C₂-C₆)-alkoxycarbonyl, (C₂-C₆)-alkylcarbonyl,    (C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,    (C₁-C₆)-haloalkylthiocarbonyl, (C₁-C₆)-alkylcarbonylamino,    aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, aminothiocarbonyl,    (C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,    (C₃-C₆)-trialkylsilyl, (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino,    (C₃-C₆)-cycloalkylamino, aminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,    di-(C₁-C₆)-alkylaminosulfonyl, sulfonylamino,    (C₁-C₆)-alkylsulfonylamino, di-(C₁-C₆)-alkylsulfonylamino, a phenyl    ring or a 3- to 6-membered aromatic, partially saturated or    saturated heterocycle, where the phenyl ring or heterocycle may in    each case optionally be mono- or polysubstituted by identical or    different substituents, and where the substituents independently of    one another may be selected from the group consisting of    (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,    (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,    (C₃-C₆)-halocycloalkyl, halogen, CN, (C═O)OH, NO₂, OH,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl, aminosulfonyl,    (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,    (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,    tri-(C₁-C₂)-alkylsilyl,    -   (referred to as not cyclically attached radical R⁸ of        configuration 1)    -   or-   R⁸ represents a 3- to 6-membered aromatic, partially saturated or    saturated heterocycle which is attached via a nitrogen atom and    where the heteroatoms are selected from the group consisting of N,    S, O, where in each case at least one carbonyl group may be present    and/or the heterocycle may in each case optionally be mono- or    polysubstituted by identical or different substituents, where the    substituents independently of one another may be selected from the    group consisting of (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,    (C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl,    (C₂-C₆)-haloalkynyl, (C₃-C₆)-halocycloalkyl, halogen, CN, (C═O)OH,    NO₂, OH, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl, aminosulfonyl,    (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl, amino,    (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, (C₃-C₆)-cycloalkylamino,    (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,    tri-(C₁-C₂)-alkylsilyl, SF₅,    -   (referred to as cyclically attached radical R⁸ of        configuration 1) n represents 0, 1 or 2.

It has additionally been found that the compounds of the formula (I)have very good efficacy as pesticides, preferably as insecticides and/oracaricides, and additionally generally have very good plantcompatibility, in particular with respect to crop plants.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

The compounds according to the invention are defined in general terms bythe formula (I). Preferred substituents or ranges of the radicals givenin the formulae mentioned above and below are illustrated hereinafter:

Configuration 2:

-   A¹ preferably represents nitrogen, ═N⁺(O⁻)— or ═C(R⁴)—,-   A² preferably represents —N—R⁵, oxygen or sulfur,-   A³ preferably represents oxygen or sulfur,-   R¹ preferably represents (C₁-C₄)-alkyl, (C₁-C₄)-hydroxyalkyl,    (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,    (C₂-C₄)-cyanoalkynyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, (C₃-C₆)-cycloalkylamino,    (C₁-C₄)-alkylcarbonylamino, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylsulfinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylcarbonyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulfonylamino,    -   or represents (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyl,        (C₂-C₄)-alkynyl, (C₃-C₆)-cycloalkyl, each of which is optionally        mono- or disubstituted by identical or different substituents        from the group consisting of aryl, hetaryl and heterocyclyl,        where aryl, hetaryl and heterocyclyl may each optionally be        mono- or disubstituted by identical or different substituents        from the group consisting of halogen, cyano, carbamoyl,        aminosulfonyl, (C₁-C₄)-alkyl, (C₃-C₄)-cycloalkyl,        (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,        (C₁-C₄)-alkylsulfimino, or-   R¹ preferably represents aryl, hetaryl or heterocyclyl, each of    which is optionally mono- or disubstituted by identical or different    substituents from the group consisting of halogen, cyano, carbamoyl,    (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-alkylsulfimino, (C₁-C₄)-alkylsulfoximino,    (C₁-C₄)-alkylcarbonyl, (C₃-C₄)-trialkylsilyl, (═O) (only in the case    of heterocyclyl) and (═O)₂ (only in the case of heterocyclyl),-   R², R³, R⁴ and R⁶ independently of one another preferably represent    hydrogen, cyano, halogen, nitro, acetyl, hydroxy, amino, SCN,    tri-(C₁-C₄)-alkylsilyl, (C₃-C₆)-cycloalkyl,    (C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,    (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-haloalkynyl, (C₂-C₄)-cyanoalkynyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-cyanoalkoxy,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylhydroxyimino,    (C₁-C₄)-alkoxyimino, (C₁-C₄)-alkyl-(C₁-C₄)-alkoxyimino,    (C₁-C₄)-haloalkyl-(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl,    (C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfonyloxy, (C₁-C₄)-alkylcarbonyl,    (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl,    (C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkyl-aminocarbonyl,    (C₁-C₄)-alkylsulfonylamino, (C₁-C₄)-alkylamino,    di-(C₁-C₄)-alkylamino, aminosulfonyl, (C₁-C₄)-alkylaminosulfonyl,    di-(C₁-C₄)-alkylaminosulfonyl, aminothiocarbonyl, NHCO—(C₁-C₄)-alkyl    ((C₁-C₄)-alkylcarbonylamino), SF₅ or    -   represent phenyl or hetaryl, each of which is optionally mono-        or disubstituted by identical or different substituents, where        (in the case of hetaryl) at least one carbonyl group may        optionally be present and/or where possible substituents are in        each case as follows: cyano, halogen, nitro, acetyl, amino,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,        (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,        (C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl,        (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl, (C₂-C₄)-cyanoalkynyl,        (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-cyanoalkoxy,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylhydroxyimino,        (C₁-C₄)-alkoxyimino, (C₁-C₄)-alkyl-(C₁-C₄)-alkoxyimino,        (C₁-C₄)-haloalkyl-(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio,        (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,        (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl,        (C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulfonyl,        (C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl,        (C₁-C₄)-alkylsulfonyloxy, (C₁-C₄)-alkylcarbonyl,        (C₁-C₄)-haloalkylcarbonyl, aminocarbonyl,        (C₁-C₄)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,        (C₁-C₄)-alkylsulfonylamino, (C₁-C₄)-alkylamino,        di-(C₁-C₄)-alkylamino, aminosulfonyl,        (C₁-C₄)-alkylaminosulfonyl, di-(C₁-C₄)-alkylaminosulfonyl,-   R⁵ preferably represents (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenyl, (C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl,    (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyl,    (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,    (C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,    (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)cycloalkyl,    (C₁-C₄)-alkyl-(C₃-C₆)cycloalkyl, halo-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylsulfinyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-haloalkylsulfonyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl or    (C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl,    -   R⁷ preferably represents hydrogen or represents (C₁-C₆)-alkyl,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,        (C₃-C₆)-cycloalkyl, (C₃-C₁₂)-cycloalkyl-(C₁-C₆)-alkyl or        (C₄-C₁₂)-bicycloalkyl, each of which is optionally mono- or        polysubstituted by identical or different substituents, where        the substituents independently of one another may be selected        from the group consisting of halogen, cyano, (C₁-C₆)-alkyl,        (C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,        (C₁-C₄)-alkylsulfonyl, (C₂-C₆)-alkoxycarbonyl,        (C₂-C₆)-alkylcarbonyl, a phenyl ring or a 3- or 6-membered        aromatic, partially saturated or saturated heterocycle, where        the phenyl ring or heterocycle may in each case optionally be        mono- or polysubstituted by identical or different substituents,        and where the substituents independently of one another may be        selected from the group consisting of (C₁-C₆)-alkyl,        (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,        (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,        (C₃-C₆)-halocycloalkyl, halogen, cyano, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,        (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,        (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl,        (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, aminocarbonyl,        (C₁-C₆-alkyl)aminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl,-   R⁸ preferably represents amino or (C₁-C₆)-alkylamino,    di-(C₁-C₄)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino,    (C₃-C₁₂)-cycloalkylamino, (C₃-C₁₂)-cycloalkyl-(C₁-C₆)-alkylamino,    (C₄-C₁₂)-bicycloalkylamino or hydrazino, each of which is optionally    mono- or polysubstituted by identical or different substituents,    where the substituents independently of one another may be selected    from the group consisting of halogen, cyano, amino, nitro, hydroxy,    (C═O)OH, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl,    (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylsulfonyl,    (C₂-C₆)-alkoxycarbonyl, (C₂-C₆)-alkylcarbonyl,    (C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonylamino,    aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,    di-(C₁-C₆)-alkylaminocarbonyl, (C₁-C₄)-alkylamino,    di-(C₁-C₄)-alkylamino, (C₃-C₆)-cycloalkylamino, aminosulfonyl,    (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,    sulfonylamino, (C₁-C₆)-alkylsulfonylamino,    di-(C₁-C₆)-alkylsulfonylamino, a phenyl ring or a 3- to 6-membered    aromatic, partially saturated or saturated heterocycle, where the    phenyl ring or heterocycle may in each case optionally be mono- or    polysubstituted by identical or different substituents, and where    the substituents independently of one another may be selected from    the group consisting of (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,    (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl,    (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, (C₃-C₆)-halocycloalkyl,    halogen, cyano, (C═O)OH, NO₂, OH, (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,    (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl, aminosulfonyl,    (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,    (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl,    -   (referred to as not cyclically attached radical R⁸ of        configuration 2)    -   or-   R⁸ furthermore preferably represents a 3- to 6-membered aromatic,    partially saturated or saturated heterocycle which is attached via a    nitrogen atom and where the heteroatoms are selected from the group    consisting of N, S, O, where in each case at least one carbonyl    group may optionally be present and/or the heterocycle may in each    case optionally be mono- or polysubstituted by identical or    different substituents, where the substituents independently of one    another may be selected from the group consisting of (C₁-C₆)-alkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,    (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,    (C₃-C₆)-halocycloalkyl, halogen, cyano, (C═O)OH, NO₂, OH,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl, aminosulfonyl,    (C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl, amino,    (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, (C₃-C₆)-cycloalkylamino,    (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl or di-(C₁-C₄)-alkylaminocarbonyl,    -   (referred to as cyclically attached radical R⁸ of configuration        2)    -   n preferably represents 0, 1 or 2.

Configuration 3:

-   A¹ particularly preferably represents nitrogen or ═C(R⁴)—,-   A² particularly preferably represents —N(R⁵)— or oxygen,-   A³ particularly preferably represents oxygen or sulfur,-   R¹ particularly preferably represents (C₁-C₄)-alkyl,    (C₁-C₄)hydroxyalkyl, (C₁-C₄)haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)haloalkynyl,    (C₃-C₆)cycloalkyl, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,    (C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl or    (C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl,-   R² particularly preferably represents hydrogen, cyano, halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl or    (C₁-C₄)-haloalkylsulfonyl,-   R³ particularly preferably represents hydrogen, halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl or    (C₁-C₄)-haloalkylsulfonyl,-   R⁴ particularly preferably represents hydrogen, halogen, cyano or    (C₁-C₄)-alkyl,-   R⁵ particularly preferably represents (C₁-C₄)-alkyl or    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,-   R⁶ particularly preferably represents hydrogen, cyano, halogen,    (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-haloalkyl,    (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylsulfinyl,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-haloalkylsulfonyl or (C₁-C₄)-alkylcarbonyl,-   R⁷ particularly preferably represents hydrogen or represents    (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, each of which is    optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen,    (C₁-C₂)-haloalkyl, cyano, phenyl and pyridyl, where phenyl and    pyridyl may each optionally be mono- or disubstituted by identical    or different substituents from the group consisting of    (C₁-C₄)-alkyl, halogen and cyano,-   R⁸ particularly preferably represents amino or (C₁-C₄)-alkylamino,    di-(C₁-C₄)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₄)-alkynylamino,    (C₃-C₆)-cycloalkylamino or hydrazino, each of which is optionally    mono- or polysubstituted by identical or different substituents,    where the substituents independently of one another may be selected    from the group consisting of halogen, cyano, (C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylsulfinyl,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkoxycarbonyl,    (C₁-C₄)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,    (C₁-C₄)-alkylcarbonylamino, aminocarbonyl,    (C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminocarbonyl, a phenyl    ring or a 3- to 6-membered aromatic, partially saturated or    saturated heterocycle, where the phenyl ring or heterocycle may in    each case optionally be mono- or polysubstituted by identical or    different substituents, and where the substituents independently of    one another may be selected from the group consisting of    (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-haloalkyl, halogen,    cyano, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl,    -   (referred to as not cyclically attached radical R⁸ of        configuration 3)    -   or-   R⁸ furthermore particularly preferably represents a 3- to 6-membered    aromatic, partially saturated or saturated heterocycle which is    attached via a nitrogen atom and where the heteroatoms are selected    from the group consisting of N, S, O, where in each case at least    one carbonyl group may be present and/or the heterocycle may in each    case optionally be mono- or polysubstituted by identical or    different substituents, where the substituents independently of one    another may be selected from the group consisting of (C₁-C₄)-alkyl,    (C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl, halogen, cyano,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,    (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl,    -   (referred to as cyclically attached radical R⁸ of configuration        3)-   n is even more preferably 0, 1 or 2.

Configuration 4:

-   A¹ very particularly preferably represents nitrogen or ═C(R⁴)—,-   A² very particularly preferably represents —N(R⁵)— or oxygen,-   A³ very particularly preferably represents oxygen or sulfur,-   R¹ very particularly preferably represents methyl, ethyl, n-propyl,    isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl,-   R² very particularly preferably represents hydrogen, methyl, ethyl,    fluorine, chlorine, bromine, cyano, fluoromethyl, difluoromethyl,    trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,    tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy,    difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio,    trifluoromethylsulfinyl or trifluoromethylsulfonyl,-   R³ very particularly preferably represents fluorine, chlorine,    fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl,    difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,    trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy,    trifluoromethylthio, trifluoromethylsulfinyl or    trifluoromethylsulfonyl,-   R⁴ very particularly preferably represents hydrogen, fluorine,    chlorine, bromine or cyano,-   R⁵ very particularly preferably represents methyl, ethyl, isopropyl,    methoxymethyl or methoxyethyl,-   R⁶ very particularly preferably represents hydrogen,-   R⁷ very particularly preferably represents hydrogen, methyl, ethyl,    isopropyl, tert-butyl, methoxymethyl or methoxyethyl,-   R⁸ very particularly preferably represents amino or represents    methylamino, dimethylamino, ethylamino, isopropylamino,    diethylamino, methylethylamino, propylamino, methylpropylamino,    ethylpropylamino, methoxyethylamino, cyanoethylamino,    methylthioethylamino, methylsulfinylethylamino,    methylsulfonylethylamino, cyclopropylamino, cyclobutylamino,    methylcyclopropylamino, methylcyclobutylamino, methylhydrazino,    dimethylhydrazino, trimethylhydrazino or phenylhydrazino,    -   (referred to as not cyclically attached radical R⁸ of        configuration 4)    -   or-   R⁸ furthermore very particularly preferably represents aziridinyl,    azetidinyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl,    thiazolidinyl, oxazolidinyl, piperidinyl, piperazinyl, morpholinyl,    thiomorpholinyl, pyrrolidonyl, imidazolidonyl, triazolinonyl,    tetrazolinonyl, piperidonyl, pyrrolyl, pyrazolyl, triazolyl,    imidazolyl or oxazolyl, attached via a nitrogen atom, in each case    optionally mono- or disubstituted by identical or different    substituents from the group consisting of methyl, ethyl,    trifluoromethyl, fluorine, chlorine, bromine and cyano,    -   (referred to as cyclically attached radical R⁸ of configuration        4)

n very particularly preferably represents 0, 1 or 2.

Configuration 5-1:

-   A¹ most preferably represents nitrogen,-   A² most preferably represents —N(R⁵)—,-   A³ most preferably represents oxygen or sulfur,-   R¹ most preferably represents ethyl,-   R² most preferably represents hydrogen, methyl or trifluoromethyl,-   R³ most preferably represents trifluoromethyl, pentafluoroethyl,    trifluoromethylthio, trifluoromethylsulfinyl or    trifluoromethylsulfonyl,-   R⁵ most preferably represents methyl,-   R⁶ most preferably represents hydrogen,-   R⁷ most preferably represents hydrogen or methyl,-   R⁸ most preferably represents amino, methylamino, dimethylamino,    ethylamino, isopropylamino, cyclopropylamino, methoxyethylamino,    cyanoethylamino, methylthioethylamino, methylsulfinylethylamino or    methylsulfonylethylamino,    -   (referred to as not cyclically attached radical R⁸ of        configuration 5-1)-   n most preferably represents 0, 1 or 2.

Configuration 5-2:

-   A¹ most preferably represents nitrogen,-   A² most preferably represents —N(R⁵)—,-   A³ most preferably represents oxygen,-   R¹ most preferably represents ethyl,-   R² most preferably represents hydrogen, methyl or trifluoromethyl,-   R³ most preferably represents trifluoromethyl, pentafluoroethyl,    trifluoromethylthio, trifluoromethylsulfinyl or    trifluoromethylsulfonyl,-   R⁵ most preferably represents methyl,-   R⁶ most preferably represents hydrogen,-   R⁷ most preferably represents hydrogen or methyl,-   R⁸ most preferably represents amino, methylamino, dimethylamino,    ethylamino, isopropylamino, cyclopropylamino, methoxyethylamino,    cyanoethylamino, methylthioethylamino, methylsulfinylethylamino or    methylsulfonylethylamino,    -   (referred to as not cyclically attached radical R⁸ of        configuration 5-2)-   R⁸ furthermore most preferably represents pyrrolidinyl, attached via    a nitrogen atom, or represents pyrazolyl, attached via a nitrogen    atom and optionally monosubstituted by bromine,    -   (referred to as cyclically attached radical R⁸ of configuration        5-2)-   n most preferably represents 0, 1 or 2.

Configuration 6-1:

-   A¹ especially represents nitrogen,-   A² especially represents —N—(R⁵)—,-   A³ especially represents oxygen,-   R¹ especially represents ethyl,-   R² especially represents hydrogen,-   R³ especially represents trifluoromethyl,-   R⁵ especially represents methyl,-   R⁶ especially represents hydrogen,-   R⁷ especially represents hydrogen,-   R⁸ especially represents methylamino (—NHCH₃), ethylamino    (—NHCH₂CH₃), isopropylamino (—NHiC₃H₇), methoxyethylamino    (—NHCH₂CH₂OCH₃), cyanoethylamino (—NHCH₂CH₂CN), methylthioethylamino    (—NHCH₂CH₂SCH₃), methylsulfinylethylamino (—NHCH₂CH₂SOCH₃) or    methylsulfonylethylamino (—NHCH₂CH₂SO₂CH₃),    -   (referred to as not cyclically attached radical R⁸ of        configuration 6-1),-   n especially represents 2.

Configuration 6-2:

-   A¹ especially represents nitrogen,-   A² especially represents —N—(R⁵)—,-   A³ especially represents oxygen,-   R¹ especially represents ethyl,-   R² especially represents hydrogen or methyl,-   R³ especially represents trifluoromethyl,-   R⁵ especially represents methyl,-   R⁶ especially represents hydrogen,-   R⁷ especially represents hydrogen or methyl,-   R⁸ especially represents methylamino (—NHCH₃), ethylamino    (—NHCH₂CH₃), isopropylamino (—NHiC₃H₇), methoxyethylamino    (—NHCH₂CH₂OCH₃), cyanoethylamino (—NHCH₂CH₂CN), methylthioethylamino    (—NHCH₂CH₂SCH₃), methylsulfinylethylamino (—NHCH₂CH₂SOCH₃),    methylsulfonylethylamino (—NHCH₂CH₂SO₂CH₃) or dimethylamino    (—N(CH₃)₂),    -   (referred to as not cyclically attached radical R⁸ of        configuration 6-2), or-   R⁸ furthermore especially represents pyrrolidinyl, attached via a    nitrogen atom, or represents pyrazolyl, attached via a nitrogen atom    and optionally monosubstituted by bromine,    -   (referred to as cyclically attached radical R⁸ of configuration        6-2)-   n especially represents 2.

Configuration 6-3:

-   A¹ especially represents nitrogen,-   A² especially represents —N—(R⁵)—,-   A³ especially represents oxygen,-   R¹ especially represents ethyl,-   R² especially represents hydrogen or methyl,-   R³ especially represents trifluoromethyl,-   R⁵ especially represents methyl,-   R⁶ especially represents hydrogen,-   R⁷ especially represents hydrogen or methyl,-   R⁸ especially represents methylamino (—NHCH₃), ethylamino    (—NHCH₂CH₃), isopropylamino (—NHiC₃H₇), methoxyethylamino    (—NHCH₂CH₂OCH₃), cyanoethylamino (—NHCH₂CH₂CN), methylthioethylamino    (—NHCH₂CH₂SCH₃), methylsulfinylethylamino (—NHCH₂CH₂SOCH₃),    methylsulfonylethylamino (—NHCH₂CH₂SO₂CH₃) or dimethylamino    (—N(CH₃)₂),    -   (referred to as not cyclically attached radical R⁸ of        configuration 6-3),-   or-   R⁸ furthermore especially represents pyrrolidinyl, attached via a    nitrogen atom, of the formula below:

or represents pyrazolyl, attached via a nitrogen atom andmonosubstituted by bromine, of the formula:

-   -   (referred to as cyclically attached radical R⁸ of configuration        6-3).

-   n especially represents 2.

In a further embodiment, the invention relates to compounds of theformula (I) in which R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A¹, A², A³ and nhave the meanings described above, in particular the meanings describedin configuration (1) or configuration (2) or configuration (3) orconfiguration (4) or configuration (5-1) or configuration (5-2) orconfiguration (6-1) or configuration (6-2) or configuration (6-3), whereR⁸ may only represent not cyclically attached radicals.

In a further embodiment, the invention relates to compounds of theformula (I) in which R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A¹, A², A³ and nhave the meanings described above, in particular the meanings describedin configuration (1) or configuration (2) or configuration (3) orconfiguration (4) or configuration (5-2) or configuration (6-2) orconfiguration (6-3), where R⁸ may only represent cyclically attachedradicals.

In a further embodiment, the invention relates to compounds of theformula (I-A)

where A¹, A³, R¹, R², R⁷, R⁸ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(2) or configuration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2) or configuration (6-1) or configuration (6-2) orconfiguration (6-3).

In a further embodiment, the invention relates to compounds of theformula (I-A)

where A¹, A³, R¹, R², R⁷, R⁸ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(2) or configuration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2) or configuration (6-1) or configuration (6-2) orconfiguration (6-3), where R⁸ may only represent not cyclically attachedradicals.

In a further embodiment, the invention relates to compounds of theformula (I-A)

where A¹, A³, R¹, R², R⁷, R⁸ and n have the meanings described above, inparticular the meanings described in configuration (1) or configuration(2) or configuration (3) or configuration (4) or configuration (5-2) orconfiguration (6-2) or configuration (6-3), where R⁸ may only representcyclically attached radicals.

In a further embodiment, the invention relates to compounds of theformula (I-B)

where A³, R⁷ and R⁸ have the meanings described above, in particular themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2) or configuration (6-1) or configuration (6-2) orconfiguration (6-3).

In a further embodiment, the invention relates to compounds of theformula (I-B)

where A³, R⁷ and R⁸ have the meanings described above, in particular themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2) or configuration (6-1) or configuration (6-2) orconfiguration (6-3), where R⁸ may only represent not cyclically attachedradicals.

In a further embodiment, the invention relates to compounds of theformula (I-B)

where A³, R⁷ and R⁸ have the meanings described above, in particular themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-2) orconfiguration (6-2) or configuration (6-3), where R⁸ may only representcyclically attached radicals.

In a further embodiment, the invention relates to compounds of theformula (I-C)

where R², R⁷ and R⁸ have the meanings described above, in particular themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2) or configuration (6-1) or configuration (6-2) orconfiguration (6-3).

In a further embodiment, the invention relates to compounds of theformula (I-C)

where R², R⁷ and R⁸ have the meanings described above, in particular themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-1) orconfiguration (5-2) or configuration (6-1) or configuration (6-2) orconfiguration (6-3), where R⁸ may only represent not cyclically attachedradicals.

In a further embodiment, the invention relates to compounds of theformula (I-C)

where R², R⁷ and R⁸ have the meanings described above, in particular themeanings described in configuration (1) or configuration (2) orconfiguration (3) or configuration (4) or configuration (5-2) orconfiguration (6-2) or configuration (6-3), where R⁸ may only representcyclically attached radicals.

In a further embodiment, the invention relates to compounds of theformula (I-D)

where R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A¹, A², A³ and n have the meaningsdescribed above, in particular the meanings described in configuration(1) or configuration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3).

In a further embodiment, the invention relates to compounds of theformula (I-D)

where R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A¹, A², A³ and n have the meaningsdescribed above, in particular the meanings described in configuration(1) or configuration (2) or configuration (3) or configuration (4) orconfiguration (5-1) or configuration (5-2) or configuration (6-1) orconfiguration (6-2) or configuration (6-3), where R⁸ may only representnot cyclically attached radicals.

In a further embodiment, the invention relates to compounds of theformula (I-D)

where R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A¹, A², A³ and n have the meaningsdescribed above, in particular the meanings described in configuration(1) or configuration (2) or configuration (3) or configuration (4) orconfiguration (5-2) or configuration (6-2) or configuration (6-3), whereR⁸ may only represent cyclically attached radicals.

In the preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group of phenyl, benzyl, naphthyl, anthryl,phenanthrenyl, and is preferably in turn phenyl,

hetaryl (synonymous with heteroaryl, including as part of a larger unit,for example hetarylalkyl) is selected from the group of furyl, thienyl,pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl,1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl,1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl,pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl,1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzisofuryl,benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl,benzothiazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl,benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl,cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl,benzotriazinyl, purinyl, pteridinyl and indolizinyl,

heterocyclyl is a saturated 4-, 5- or 6-membered ring containing 1 or 2nitrogen atoms and/or one oxygen atom and/or one sulfur atom, forexample azetidinyl, pyrrolidinyl, piperidinyl, oxetanyl,tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, thietanyl,tetrahydrothiophenyl, tetrahydrothiopyranyl, piperazinyl, morpholinyland thiomorpholinyl.

In the particularly preferred definitions, unless stated otherwise,

halogen is selected from the group of fluorine, chlorine, bromine andiodine, preferably in turn from the group of fluorine, chlorine andbromine,

aryl (including as part of a larger unit, for example arylalkyl) isselected from the group of phenyl, benzyl, naphthyl, anthryl,phenanthrenyl, and is preferably in turn phenyl,

hetaryl (including as part of a larger unit, for example hetarylalkyl)is selected from the group consisting of pyridyl, pyrimidyl, pyrazinyl,pyridazinyl, pyrazolyl, imidazolyl, triazolyl, thiazolyl and tetrazolyl,

heterocyclyl is selected from the group consisting of oxetanyl,tetrahydrofuryl and piperazinyl.

In the context of the present invention, unless defined differentlyelsewhere, the term “alkyl”, either on its own or else in combinationwith further terms, for example haloalkyl, is understood to mean aradical of a saturated, aliphatic hydrocarbon group which has 1 to 12carbon atoms and may be branched or unbranched. Examples of C₁-C₁₂-alkylradicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl,1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl,n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl. Amongthese alkyl radicals, particular preference is given to C₁-C₆-alkylradicals. Special preference is given to C₁-C₄-alkyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkenyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkenylradical which has at least one double bond, for example vinyl, allyl,1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl,1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1,3-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyland 1,4-hexadienyl. Among these, preference is given to C₂-C₆-alkenylradicals and particular preference to C₂-C₄-alkenyl radicals.

According to the invention, unless defined differently elsewhere, theterm “alkynyl”, either on its own or else in combination with furtherterms, is understood to mean a straight-chain or branched C₂-C₁₂-alkynylradical which has at least one triple bond, for example ethynyl,1-propynyl and propargyl. Among these, preference is given toC₃-C₆-alkynyl radicals and particular preference to C₃-C₄-alkynylradicals. The alkynyl radical may also contain at least one double bond.

According to the invention, unless defined differently elsewhere, theterm “cycloalkyl”, either on its own or else in combination with furtherterms, is understood to mean a C₃-C₈-cycloalkyl radical, for examplecyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl. Among these, preference is given to C₃-C₆-cycloalkylradicals.

The term “alkoxy”, either on its own or else in combination with furtherterms, for example haloalkoxy, is understood in the present case to meanan O-alkyl radical, where the term “alkyl” is as defined above.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated, up to the maximum number of possible substituents. Inthe case of polyhalogenation, the halogen atoms may be identical ordifferent. Halogen here is fluorine, chlorine, bromine or iodine,especially fluorine, chlorine or bromine.

Unless stated otherwise, optionally substituted radicals may be mono- orpolysubstituted, where the substituents in the case of polysubstitutionsmay be the same or different.

The radical definitions or illustrations given in general terms orlisted within ranges of preference apply correspondingly to end productsand to starting materials and intermediates. These radical definitionscan be combined with one another as desired, i.e. including combinationsbetween the respective ranges of preference.

Preference according to the invention is given to using compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to usingcompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to usingcompounds of the formula (I) which contain a combination of thedefinitions listed above as being very particularly preferred.

Most preference according to the invention is given to using compoundsof the formula (I) which contain a combination of the meanings listedabove as being most preferable.

Especially used according to the invention are compounds of the formula(I) which contain a combination of the meanings listed above as beingespecially emphasized.

Depending on the nature of the substituents, the compounds of theformula (I) may take the form of geometric and/or optically activeisomers or corresponding isomer mixtures in different compositions.These stereoisomers are, for example, enantiomers, diastereomers,atropisomers or geometric isomers. The invention therefore encompassespure stereoisomers and any desired mixtures of these isomers.

The inventive compounds of the formula (I) can be obtained by theprocesses shown in the following schemes:

The radicals R¹, R², R³, R⁶, R⁷, R⁸, A¹, A² and A³ have the meaningsdescribed above and X¹ and X² represent halogen.

Step a)

The compounds of the formula (VIII) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,576,335 by the reaction ofcompounds of the formula (II) with a carboxylic acid of the formula(VII) in the presence of a condensing agent or a base.

Compounds of the formula (II) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in US2003/69257 or WO2006/65703.

Carboxylic acids of the formula (VII) are either commercially availableor can be prepared by known methods, for example analogously to theprocesses described in US2010/234604, WO2012/61926 or Bioorganic andMedicinal Chemistry Letters, 18 (2008), 5023-5026.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (VII) can be effected neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogen compounds, forexample pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide.

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Particularpreference is given here to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium hydrogencarbonate, potassium hydrogencarbonate.

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of 0° C. to 180°C.; with preference, the reaction is carried out at standard pressureand temperatures of 20 to 140° C.

Step b)

The compounds of the formula (IX) can be prepared by condensing theintermediates of the formula (VIII), for example analogously to theprocesses described in WO2012/86848.

The conversion to compounds of the formula (IX) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction can be carried out in the presence of a condensing agent,an acid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulfonic acids such as para-toluenesulfonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

The compounds of the formula (XI) can be prepared by reacting thecompounds of the formula (IX) with the compounds of the formula (X) inthe presence of a base.

Mercaptan derivatives of the formula (X), for example methyl mercaptan,ethyl mercaptan or isopropyl mercaptan, are either commerciallyavailable or can be prepared by known methods, for example analogouslyto the processes described in US2006/25633, US2006/111591, U.S. Pat. No.2,820,062, Chemical Communications, 13 (2000), 1163-1164 or Journal ofthe American Chemical Society, 44 (1922), p. 1329.

The conversion to compounds of the formula (XI) can be effected neat orin a solvent, preference being given to conducting the reaction in asolvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given here to caesium carbonate, sodiumcarbonate and potassium carbonate. Further suitable bases are alkalimetal hydrides, for example sodium hydride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step d)

The compounds of the formula (XII) can be prepared by oxidizing thecompounds of the formula (XI). The oxidation is generally carried out ina solvent selected from customary solvents which are inert under theprevailing reaction conditions. Preference is given to halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such asmethanol or ethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide,meta-chloroperbenzoic acid or sodium periodate.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step e)

The compounds of the formula (XIII) can be prepared by oxidizing thecompounds of the formula (XII). The oxidation is generally carried outin a solvent. Preference is given to halogenated hydrocarbons, forexample dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; alcohols such as methanol orethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step f)

The compounds of the formula (XIII) can also be prepared in a one-stepprocess by oxidizing the compounds of the formula (XI). The oxidation isgenerally carried out in a solvent. Preference is given to halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such asmethanol or ethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step g)

The compounds of the formula (XV) can be prepared by reacting compoundsof the formula (XIII) with compounds of the formula (XIV).

Compounds of the formula (XIV) are either commercially available or canbe prepared by known methods.

The conversion to compounds of the formula (XV) is generally carried outin a solvent. Preference is given to ethers such as, for example,tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycoldimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatichydrocarbons such as toluene, xylene, halogenated hydrocarbons such as,for example, dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene, aprotic polar solvents such as, forexample, N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide,or esters such as, for example, ethyl acetate, or nitriles such asacetonitrile.

The reaction can be carried out in the presence of a base. Examples ofsuitable bases are nitrogen heterocycles such as pyridine, picoline,2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary aminessuch as triethylamine and N,N-diisopropylethylamine; or inorganic basessuch as potassium phosphate, potassium carbonate and sodium hydride.

Step h)

The compounds of the formula (I′) can be prepared by reacting compoundsof the formula (XVI) with compounds of the formula (XV).

Compounds of the formulae (XVI) are either commercially available or canbe prepared by known methods.

The conversion to compounds of the formula (I′) is generally carried outin a solvent. Preference is given to ethers such as, for example,tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycoldimethyl ether, halogenated hydrocarbons such as, for example,dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane orchlorobenzene, aromatic hydrocarbons such as toluene, xylene, esterssuch as, for example, ethyl acetate, nitriles such as acetonitrile,aprotic polar solvents such as, for example, N,N-dimethylformamide,N-methylpyrrolidone, dimethyl sulfoxide or nitrogenous heterocycles suchas pyridine or quinoline.

The reaction can be carried out in the presence of a condensing agent.Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) and1,3-dicyclohexylcarbodiimide.

The reaction can be carried out in the presence of a suitable catalyst.An example of a suitable catalyst is 1-hydroxybenzotriazole.

The compounds of the formula (I′) can also be prepared by reactingcompounds of the formula (XVII) with compounds of the formula (XV).

Compounds of the formula (XVII) are either commercially available or canbe prepared by known methods.

The conversion to compounds of the formula (I′) is generally carried outin a solvent. Preference is given to ethers such as, for example,tetrahydrofuran, methyl tert-butyl ether, dioxane, ethylene glycoldimethyl ether, aliphatic hydrocarbons such as hexane, heptane, aromatichydrocarbons such as toluene, xylene, halogenated hydrocarbons such as,for example, dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene, aprotic polar solvents such as, forexample, N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide,or esters such as, for example, ethyl acetate, or nitriles such asacetonitrile.

The reaction can be carried out in the presence of a base. Examples ofsuitable bases are nitrogen heterocycles such as pyridine,dimethylaminopyridine, picoline, 2,6-lutidine,1,8-diazabicyclo[5.4.0]-7-undecene (DBU); tertiary amines such astriethylamine and N,N-diisopropylethylamine; or inorganic bases such aspotassium carbonate and sodium hydride.

The reaction according to steps g) and h) can also take place startingfrom compounds of the formula (XI) or the formula (XII).

The radicals R¹, R², R³, R⁶, A¹ and A² have the meanings described aboveand X¹ represents halogen.

Step a)

The compounds of the formula (XVIII) can be prepared analogously toWO2015/002211 by reacting the compounds of the formula (XI, XII or XIII)with sodium azide.

The conversion to compounds of the formula (XVIII) is usually carriedout in a solvent, preference being given to carrying out the reaction ina solvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers such as,for example, tetrahydrofuran, ethylene glycol dimethyl ether, dioxane,aprotic polar solvents such as, for example, N,N-dimethylformamide,N-methylpyrrolidone, dimethyl sulfoxide, or alcohols such as methanol orethanol.

Step b)

The compounds of the formula (XIX) can be prepared by reducing theintermediates of the formula (XVIII), for example analogously to theprocesses described in WO2015/002211.

Examples of suitable reducing agents are triphenylphosphine,tributylphosphine, tin(III) chloride and zinc.

The conversion to compounds of the formula (XIX) is generally carriedout in a solvent. Preference is given to ethers such as, for example,tetrahydrofuran, ethylene glycol dimethyl ether, dioxane, aliphatichydrocarbons such as hexane, heptane, aromatic hydrocarbons such astoluene, xylene, halogenated hydrocarbons such as, for example,dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane orchlorobenzene, aprotic polar solvents such as, for example,N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, oralcohols such as methanol or ethanol.

If required, an acid such as, for example, hydrochloric acid or aceticacid may be added to the reaction.

The further conversion of the compounds of the formula (XIX) tocompounds of the formula (I) is effected analogously to process A.

The radicals R¹, R², R³, R⁶, A¹ and A² have the meanings described aboveand X² represents halogen.

Step a)

The compounds of the formula (XXI) can be prepared in analogy to theprocess described in U.S. Pat. No. 5,576,335 by the reaction ofcompounds of the formula (II) with a carboxylic acid of the formula (XX)in the presence of a condensing agent or a base.

Compounds of the formula (II) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in US2003/69257 or WO2006/65703.

Carboxylic acids of the formula (XX) are either commercially availableor can be prepared by known methods, for example analogously to theprocesses described in US2010/234604, WO2012/61926 or Bioorganic andMedicinal Chemistry Letters, 18 (2008), 5023-5026.

The reaction of the compounds of the formula (II) with carboxylic acidsof the formula (XX) can be effected neat or in a solvent, preferencebeing given to conducting the reaction in a solvent selected fromcustomary solvents that are inert under the prevailing reactionconditions. Preference is given to ethers, for example diisopropylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; nitriles, forexample acetonitrile or propionitrile; aromatic hydrocarbons, forexample toluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide or N-methylpyrrolidone, or nitrogen compounds, forexample pyridine.

Suitable condensing agents are, for example, carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide.

Suitable bases are inorganic bases which are typically used in suchreactions. Preference is given to using bases selected by way of examplefrom the group consisting of acetates, phosphates, carbonates andhydrogencarbonates of alkali metals or alkaline earth metals. Particularpreference is given here to sodium acetate, sodium phosphate, potassiumphosphate, caesium carbonate, sodium carbonate, potassium carbonate,sodium hydrogencarbonate, potassium hydrogencarbonate.

The reaction can be effected under reduced pressure, at standardpressure or under elevated pressure and at temperatures of 0° C. to 180°C.; with preference, the reaction is carried out at standard pressureand temperatures of 20 to 140° C.

Step b)

The compounds of the formula (XXII) can be prepared by condensing thecompounds of the formula (XXI), for example analogously to the processesdescribed in WO2012/86848.

The conversion to compounds of the formula (XXII) can be carried outneat or in a solvent, preference being given to conducting the reactionin a solvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons,for example dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; nitriles, for example acetonitrileor propionitrile; aromatic hydrocarbons, for example toluene or xylene;aprotic polar solvents, for example N,N-dimethylformamide orN-methylpyrrolidone, or nitrogen compounds, for example pyridine.

The reaction can be carried out in the presence of a condensing agent,an acid, a base or a chlorinating agent.

Examples of suitable condensing agents are carbodiimides such as1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) or1,3-dicyclohexylcarbodiimide; anhydrides such as acetic anhydride,trifluoroacetic anhydride; a mixture of triphenylphosphine, a base andcarbon tetrachloride, or a mixture of triphenylphosphine and an azodiester, for example diethylazodicarboxylic acid.

Examples of suitable acids which can be used in the reaction describedare sulfonic acids such as para-toluenesulfonic acid; carboxylic acidssuch as acetic acid, or polyphosphoric acids.

Examples of suitable bases are nitrogen heterocycles such as pyridine,picoline, 2,6-lutidine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU);tertiary amines such as triethylamine and N,N-diisopropylethylamine;inorganic bases such as potassium phosphate, potassium carbonate andsodium hydride.

An example of a suitable chlorinating agent is phosphorus oxychloride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step c)

The compounds of the formula (XXIII) can be prepared by reacting thecompounds of the formula (XXII) with the compounds of the formula (X) inthe presence of a base.

Mercaptan derivatives of the formula (X), for example methyl mercaptan,ethyl mercaptan or isopropyl mercaptan, are either commerciallyavailable or can be prepared by known methods, for example analogouslyto the processes described in US2006/25633, US2006/111591, U.S. Pat. No.2,820,062, Chemical Communications, 13 (2000), 1163-1164 or Journal ofthe American Chemical Society, 44 (1922), p. 1329.

The conversion to compounds of the formula (XXIII) can be carried outneat or in a solvent, preference being given to conducting the reactionin a solvent selected from customary solvents that are inert under theprevailing reaction conditions. Preference is given to ethers, forexample diisopropyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, tert-butyl methyl ether; nitriles, for exampleacetonitrile or propionitrile; aromatic hydrocarbons, for exampletoluene or xylene; aprotic polar solvents, for exampleN,N-dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.

Examples of suitable bases are inorganic bases from the group consistingof acetates, phosphates and carbonates of alkali metals or alkalineearth metals. Preference is given here to caesium carbonate, sodiumcarbonate and potassium carbonate. Further suitable bases are alkalimetal hydrides, for example sodium hydride.

The reaction can be conducted under reduced pressure, at standardpressure or under elevated pressure, and at temperatures of 0° C. to200° C.

Step d)

The compounds of the formula (XXIV) can be prepared by oxidizing thecompounds of the formula (XXIII). The oxidation is generally carried outin a solvent selected from customary solvents which are inert under theprevailing reaction conditions. Preference is given to halogenatedhydrocarbons, for example dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such asmethanol or ethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide,meta-chloroperbenzoic acid or sodium periodate.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

Step e)

The compounds of the formula (XXV) can be prepared by oxidizing thecompounds of the formula (XXIV). The oxidation is generally carried outin a solvent. Preference is given to halogenated hydrocarbons, forexample dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane or chlorobenzene; alcohols such as methanol orethanol; formic acid, acetic acid, propionic acid or water.

Examples of suitable oxidizing agents are hydrogen peroxide andmeta-chloroperbenzoic acid.

The reaction can be carried out under reduced pressure, at atmosphericpressure or under elevated pressure, and at temperatures of −20° C. to120° C.

The further conversion of the compounds of the formula (XXV) or of theformula (XXIV) or of the formula (XXIII) to compounds of the formula (I)is carried out analogously to process A.

The radicals R¹, R², R³, R⁶, R⁸, A¹, A² and A³ have the meaningsdescribed above and X¹ represents halogen.

Step a)

The compounds of the formula (I′) can be prepared in a one-step processby reacting the compounds of the formula (XIII) with compounds of theformula (XXVI) analogously to the processes described in Synthesis,(2005), 915-924 or Organic Letters, 11 (2009), 947-950.

Compounds of the formula (XXVI) are either commercially available or canbe prepared by known methods, for example analogously to the processesdescribed in Houben-Weyl, Methoden der organischen Chemie [Methods ofOrganic Chemistry], volume XVI/2, 4th edition.

The conversion to compounds of the formula (I′) is generally carried outin a solvent in the presence of a base. Preferred solvents are etherssuch as dioxane or ethylene glycol dimethyl ether, preferred bases are,for example, caesium carbonate, potassium phosphate or sodiumtert-butoxide.

The conversion to compounds of the formula (I′) is generally carried outin the presence of a catalyst and a ligand. Suitable for use ascatalysts are palladium complexes such as, for example,tris(dibenzylideneacetone)dipalladium(0) or palladium acetate and theligands employed are generally organophosphane compounds such as, forexample, bis(diphenylphosphine)-9,9-dimethylxanthene (xanthphos).

Methods and Uses

The invention also relates to methods for controlling animal pests, inwhich compounds of the formula (I) are allowed to act on animal pestsand/or their habitat. The control of the animal pests is preferablycarried out in agriculture and forestry, and in material protection.This preferably excludes methods for surgical or therapeutic treatmentof the human or animal body and diagnostic methods carried out on thehuman or animal body.

The invention further relates to the use of the compounds of the formula(I) as pesticides, especially crop protection compositions.

In the context of the present application, the term “pesticide” in eachcase also always encompasses the term “crop protection composition”.

The compounds of the formula (I), given good plant tolerance, favourableendotherm toxicity and good environmental compatibility, are suitablefor protecting plants and plant organs against biotic and abiotic stressfactors, for increasing harvest yields, for improving the quality of theharvested material and for controlling animal pests, especially insects,arachnids, helminths, especially nematodes and molluscs, which areencountered in agriculture, in horticulture, in animal husbandry, inaquatic cultures, in forests, in gardens and leisure facilities, in theprotection of stored products and of materials, and in the hygienesector.

In the context of the present patent application, the term “hygiene”should be understood to mean any and all measures, provisions andprocedures which have the aim of preventing diseases, especiallyinfection diseases, and which serve to protect the health of humans andanimals and/or protect the environment and/or maintain cleanliness.According to the invention, this especially includes measures forcleaning, disinfection and sterilization, for example of textiles orhard surfaces, especially surfaces made of glass, wood, cement,porcelain, ceramic, plastic or else metal(s), in order to ensure thatthese are free of hygiene pests and/or their secretions. The scope ofprotection of the invention in this regard preferably excludes surgicalor therapeutic treatment procedures to be applied to the human body orthe bodies of animals, and diagnostic procedures which are carried outon the human body or the bodies of animals.

The term “hygiene sector” covers all areas, technical fields andindustrial applications in which these hygiene measures, provisions andprocedures are important, for example with regard to hygiene inkitchens, bakeries, airports, bathrooms, swimming pools, departmentstores, hotels, hospitals, stables, animal keeping, etc.

The term “hygiene pest” should therefore be understood to mean one ormore animal pests whose presence in the hygiene sector is problematic,especially for reasons of health. A main aim is therefore that ofavoiding, or limiting to a minimum degree, the presence of hygiene pestsand/or the exposure to these in the hygiene sector. This can especiallybe achieved through the use of a pesticide which can be used both forprevention of infestation and for prevention of an existing infestation.It is also possible to use formulations which prevent or reduce exposureto pests. Hygiene pests include, for example, the organisms mentionedbelow.

The term “hygiene protection” thus covers all acts by which thesehygiene measures, provisions and procedures are maintained and/orimproved.

The compounds of the formula (I) can preferably be used as pesticides.They are active against normally sensitive and resistant species andalso against all or specific stages of development. The abovementionedpests include:

pests from the phylum of the Arthropoda, in particular from the class ofthe Arachnida, for example Acarus spp., Acarus spp., e.g. Acarus siro,Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., e.g. Aculusfockeui, Aculus schlechtendali, Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., e.g.Brevipalpus phoenicis, Bryobia graminum, Bryobia praetiosa, Centruroidesspp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoidespteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychusspp., e.g. Eotetranychus hicoriae, Epitrimerus pyri, Eutetranychus spp.,e.g. Eutetranychus banksi, Eriophyes spp., e.g. Eriophyes pyri,Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., e.g.Hemitarsonemus latus (=Polyphagotarsonemus latus), Hyalomma spp., Ixodesspp., Latrodectus spp., Loxosceles spp., Neutrombicula autumnalis,Nuphersa spp., Oligonychus spp., e.g. Oligonychus coffeae, Oligonychusconiferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychusmangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychusyothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., e.g.Panonychus citri (=Metatetranychus citri), Panonychus ulmi(=Metatetranychus ulmi), Phyllocoptruta oleivora, Platytetranychusmultidigituli, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalusspp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus,Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., e.g.Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., e.g.Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychusturkestani, Tetranychus urticae, Trombicula alfreddugesi, Vaejovis spp.,Vasates lycopersici;

from the class of the Chilopoda, for example Geophilus spp., Scutigeraspp.;

from the order or the class of the Collembola, for example onychiurusArmatus; Sminthurus viridis;

from the class of the Diplopoda, for example Blaniulus guttulatus;

from the class of the Insecta, for example from the order of theBlattodea, e.g. Blatta orientalis, Blattella asahinai, Blattellagermanica, Leucophaea maderae, Loboptera decipiens, Neostylopygarhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., e.g.Periplaneta americana, Periplaneta australasiae, Pycnoscelussurinamensis, Supella longipalpa;

from the order of the Coleoptera, for example Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Aethina tumida, Agelasticaalni, Agrilus spp., e.g. Agrilus planipennis, Agrilus coxalis, Agrilusbilineatus, Agrilus anxius, Agriotes spp., e.g. Agriotes linneatus,Agriotes mancus, Alphitobius diaperinus, Amphimallon solstitialis,Anobium punctatum, Anoplophora spp., e.g. Anoplophora glabripennis,Anthonomus spp., e.g. Anthonomus grandis, Anthrenus spp., Apion spp.,Apogonia spp., Atomaria spp., e.g. Atomaria linearis, Attagenus spp.,Baris caerulescens, Bruchidius obtectus, Bruchus spp., e.g. Bruchuspisorum, Bruchus rufimanus, Cassida spp., Cerotoma trifurcata,Ceutorrhynchus spp., e.g. Ceutorrhynchus assimilis, Ceutorrhynchusquadridens, Ceutorrhynchus rapae, Chaetocnema spp., e.g. Chaetocnemaconfinis, Chaetocnema denticulata, Chaetocnema ectypa, Cleonus mendicus,Conoderus spp., Cosmopolites spp., e.g. Cosmopolites sordidus,Costelytra zealandica, Ctenicera spp., Curculio spp., e.g. Curculiocaryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi,Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptorhynchus lapathi,Cryptorhynchus mangiferae, Cylindrocopturus spp., Cylindrocopturusadspersus, Cylindrocopturus furnissi, Dendroctonus spp., e.g.Dendroctonus ponderosae, Dermestes spp., Diabrotica spp., e.g.Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctatahowardi, Diabrotica undecimpunctata undecimpunctata, Diabroticavirgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp.,Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp.,e.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., e.g.Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrixsubcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides,Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyxspp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomecessquamosus, Hypothenemus spp., e.g. Hypothenemus hampei, Hypothenemusobscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasiodermaserricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsadecemlineata, Leucoptera spp., e.g. Leucoptera coffeella, Lissorhoptrusoryzophilus, Listronotus (=Hyperodes) spp., Lixus spp., Luperodes spp.,Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., e.g. Megacyllenerobiniae, Megascelis spp., Melanotus spp., e.g. Melanotus longulusoregonensis, Meligethes aeneus, Melolontha spp., e.g. Melolonthamelolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus,Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctesrhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchusspp., e.g. Otiorhynchus cribricollis, Otiorhynchus ligustici,Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus,Oulema spp., e.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda,Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotretaspp., e.g. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotretaramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp.,Prostephanus truncatus, Psylliodes spp., e.g. Psylliodes affinis,Psylliodes chrysocephala, Psylliodes punctulata, Ptinus spp., Rhizobiusventralis, Rhizopertha dominica, Rhynchophorus spp., Rhynchophorusferrugineus, Rhynchophorus palmarum, Scolytus spp., e.g. Scolytusmultistriatus, Sinoxylon perforans, Sitophilus spp., e.g. Sitophilusgranarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais,Sphenophorus spp., Stegobium paniceum, Sternechus spp., e.g. Sternechuspaludatus, Symphyletes spp., Tanymecus spp., e.g. Tanymecusdilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor,tenebrioides mauretanicus, Tribolium spp., e.g. Tribolium audax,Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp.,Xylotrechus spp., Zabrus spp., e.g. Zabrus tenebrioides; from the orderof the dermaptera, for example Anisolabis maritime, Forficulaauricularia, Labidura riparia;

from the order of the Diptera, for example Aedes spp., e.g. Aedesaegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp.,e.g. Agromyza frontella, Agromyza parvicornis, Anastrepha spp.,Anopheles spp., e.g. Anopheles quadrimaculatus, Anopheles gambiae,Asphondylia spp., Bactrocera spp., e.g. Bactrocera cucurbitae,Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphoraerythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp.,Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp.,Contarinia spp., e.g. Contarinia johnsoni, Contarinia nasturtii,Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola,Contarinia tritici, Cordylobia anthropophaga, Cricotopus sylvestris,Culex spp., e.g. Culex pipiens, Culex quinquefasciatus, Culicoides spp.,Culiseta spp., Cuterebra spp., Dacus oleae, Dasineura spp., e.g.Dasineura brassicae, Delia spp., e.g. Delia antiqua, Delia coarctata,Delia florilega, Delia platura, Delia radicum, Dermatobia hominis,Drosophila spp., e.g. Drosphila melanogaster, Drosophila suzukii,Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp.,Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola,Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., e.g.Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae, Luciliaspp., e.g. Lucilia cuprina, Lutzomyia spp., Mansonia spp., Musca spp.,e.g. Musca domestica, Musca domestica vicina, Oestrus spp., Oscinellafrit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomya oderPegomyia spp., e.g. Pegomya betae, Pegomya hyoscyami, Pegomya rubivora,Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Platypareapoeciloptera, Prodiplosis spp., Psila rosae, Rhagoletis spp., e.g.Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletisindifferens, Rhagoletis mendax, Rhagoletis pomonella, Sarcophaga spp.,Simulium spp., e.g. Simulium meridionale, Stomoxys spp., Tabanus spp.,Tetanops spp., Tipula spp., e.g. Tipula paludosa, Tipula simplex,Toxotrypana curvicauda;

from the order of the Hemiptera, for example Acizzia acaciaebaileyanae,Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosiponspp., e.g. Acyrthosiphon pisum, Acrogonia spp., Aeneolamia spp.,Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobusbarodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrascaspp., e.g. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui,Aonidiella spp., e.g. Aonidiella aurantii, Aonidiella citrina,Aonidiella inornata, Aphanostigma piri, Aphis spp., e.g. Aphiscitricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines,Aphis gossypii, Aphis hederae, Aphis illinoisensis, Aphis middletoni,Aphis nasturtii, Aphis nerii, Aphis pomi, Aphis spiraecola, Aphisviburniphila, Arboridia apicalis, Arytainilla spp., Aspidiella spp.,Aspidiotus spp., e.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani,Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae,Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae,Cacopsylla spp., e.g. Cacopsylla pyricola, Calligypona marginata,Capulinia spp., Cameocephala fulgida, Ceratovacuna lanigera, Cercopidae,Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis,Chlorita onukii, Chondracris rosea, Chromaphis juglandicola,Chrysomphalus aonidum, Chrysomphalus ficus, Cicadulina mbila,Coccomytilus halli, Coccus spp., e.g. Coccus hesperidum, Coccuslongulus, Coccus pseudomagnoliarum, Coccus viridis, Cryptomyzus ribis,Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodeschittendeni, Dialeurodes citri, Diaphorina citri, Diaspis spp.,Diuraphis spp., Doralis spp., Drosicha spp., Dysaphis spp., e.g.Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae, Dysmicoccusspp., Empoasca spp., e.g. Empoasca abrupta, Empoasca fabae, Empoascamaligna, Empoasca solana, Empoasca stevensi, Eriosoma spp., e.g.Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola, Erythroneuraspp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisiaspp., Fiorinia spp., Furcaspis oceanica, Geococcus coffeae, Glycaspisspp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodiscacoagulata, Hyalopterus arundinis, Hyalopterus pruni, Icerya spp., e.g.Icerya purchasi, Idiocerus spp., Idioscopus spp., Laodelphaxstriatellus, Lecanium spp., e.g. Lecanium corni (=Parthenolecaniumcorni), Lepidosaphes spp., e.g. Lepidosaphes ulmi, Lipaphis erysimi,Lopholeucaspis japonica, Lycorma delicatula, Macrosiphum spp., e.g.Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae,Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiellaspp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis,Monelliopsis pecanis, Myzus spp., e.g. Myzus ascalonicus, Myzus cerasi,Myzus ligustri, Myzus omatus, Myzus persicae, Myzus nicotianae,Nasonovia ribisnigri, Neomaskellia spp., Nephotettix spp., e.g.Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra,Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxyachinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., e.g.Paratrioza cockerelli, Parlatoria spp., Pemphigus spp., e.g. Pemphigusbursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp.,Phenacoccus spp., e.g. Phenacoccus madeirensis, Phloeomyzus passerinii,Phorodon humuli, Phylloxera spp., e.g. Phylloxera devastatrix,Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., e.g.Planococcus citri, Prosopidopsylla flava, Protopulvinaria pyriformis,Pseudaulacaspis pentagona, Pseudococcus spp., e.g. Pseudococcuscalceolariae, Pseudococcus comstocki, Pseudococcus longispinus,Pseudococcus maritimus, Pseudococcus vibumi, Psyllopsis spp., Psyllaspp., e.g. Psylla buxi, Psylla mali, Psylla pyri, Pteromalus spp.,Pulvinaria spp., Pyrilla spp., Quadraspidiotus spp., e.g.Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis,Quadraspidiotus perniciosus, Quesada gigas, Rastrococcus spp.,Rhopalosiphum spp., e.g. Rhopalosiphum maidis, Rhopalosiphumoxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale, Saissetiaspp., e.g. Saissetia coffeae, Saissetia miranda, Saissetia neglecta,Saissetia oleae, Scaphoideus titanus, Schizaphis graminum, Selenaspidusarticulatus, Sipha flava, Sitobion avenae, Sogata spp., Sogatellafurcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae,Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae,Tomaspis spp., Toxoptera spp., e.g. Toxoptera aurantii, Toxopteracitricidus, Trialeurodes vaporariorum, Trioza spp., e.g. Triozadiospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.;

from the suborder of the Heteroptera, for example Aelia spp., Anasatristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp.,Campylomma livida, Cavelerius spp., Cimex spp., e.g. Cimex adjunctus,Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp.,Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocorishewetti, Dysdercus spp., Euschistus spp., e.g. Euschistus heros,Euschistus servus, Euschistus tristigmus, Euschistus variolarius,Eurydema spp., Eurygaster spp., Halyomorpha halys, Heliopeltis spp.,Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis,Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp., e.g.Lygocoris pabulinus, Lygus spp., e.g. Lygus elisus, Lygus hesperus,Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae,Monalonion atratum, Nezara spp., e.g. Nezara viridula, Nysius spp.,Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., e.g.Piezodorus guildinii, Psallus spp., Pseudacysta persea, Rhodnius spp.,Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp.,Stephanitis nashi, Tibraca spp., Triatoma spp.;

from the order of the Hymenoptera, for example Acromyrmex spp., Athaliaspp., e.g. Athalia rosae, Atta spp., Camponotus spp., Dolichovespulaspp., Diprion spp., e.g. Diprion similis, Hoplocampa spp., e.g.Hoplocampa cookei, Hoplocampa testudinea, Lasius spp., Linepithema(Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp.,Paravespula spp., Plagiolepis spp., Sirex spp., e.g. Sirex noctilio,Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp.,Vespa spp., e.g. Vespa crabro, Wasmannia auropunctata, Xeris spp.;

from the order of the Isopoda, for example Armadillidium vulgare,Oniscus asellus, Porcellio scaber; from the order of the Isoptera, forexample Coptotermes spp., e.g. Coptotermes formosanus, Cornitermescumulans, Cryptotermes spp., Incisitermes spp., Kalotermes spp.,Microtermes obesi, Nasutitermis spp., Odontotermes spp., Porotermesspp., Reticulitermes spp., e.g. Reticulitermes flavipes, Reticulitermeshesperus;

from the order of the Lepidoptera, for example Achroia grisella,Acronicta major, Adoxophyes spp., e.g. Adoxophyes orana, Aedialeucomelas, Agrotis spp., e.g. Agrotis segetum, Agrotis ipsilon, Alabamaspp., e.g. Alabama argillacea, Amyelois transitella, Anarsia spp.,Anticarsia spp., e.g. Anticarsia gemmatalis, Argyroploce spp.,Autographa spp., Barathra brassicae, Blastodacna atra, Borbo cinnara,Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoeciaspp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella,Carposina niponensis, Cheimatobia brumata, Chilo spp., e.g. Chiloplejadellus, Chilo suppressalis, Choreutis pariana, Choristoneura spp.,Chrysodeixis chalcites, Clysia ambiguella, Cnaphalocerus spp.,Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp.,Conotrachelus spp., Copitarsia spp., Cydia spp., e.g. Cydia nigricana,Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp.,Diatraea saccharalis, Dioryctria spp., e.g. Dioryctria zimmermani,Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldanasaccharina, Ephestia spp., e.g. Ephestia elutella, Ephestia kuehniella,Epinotia spp., Epiphyas postvittana, Erannis spp., Erschoviellamusculana, Etiella spp., Eudocima spp., Eulia spp., Eupoeciliaambiguella, Euproctis spp., e.g. Euproctis chrysorrhoea, Euxoa spp.,Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp.,e.g. Grapholita molesta, Grapholita prunivora, Hedylepta spp.,Helicoverpa spp., e.g. Helicoverpa armigera, Helicoverpa zea, Heliothisspp., e.g. Heliothis virescens, Hofmannophila pseudospretella,Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoriaflavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta,Leucinodes orbonalis, Leucoptera spp., e.g. Leucoptera coffeella,Lithocolletis spp., e.g. Lithocolletis blancardella, Lithophaneantennata, Lobesia spp., e.g. Lobesia botrana, Loxagrotis albicosta,Lymantria spp., e.g. Lymantria dispar, Lyonetia spp., e.g. Lyonetiaclerkella, Malacosoma neustria, Maruca testulalis, Mamestra brassicae,Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata,Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Omphisa spp.,Operophtera spp., Oria spp., Orthaga spp., Ostrinia spp., e.g. Ostrinianubilalis, Panolis flammea, Parnara spp., Pectinophora spp., e.g.Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., e.g.Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp.,e.g. Phyllonorycter blancardella, Phyllonorycter crataegella, Pierisspp., e.g. Pieris rapae, Platynota stultana, Plodia interpunctella,Plusia spp., Plutella xylostella (=Plutella maculipennis), Podesia spp.,e.g. Podesia syringae, Prays spp., Prodenia spp., Protoparce spp.,Pseudaletia spp., e.g. Pseudaletia unipuncta, Pseudoplusia includens,Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., e.g. Schoenobiusbipunctifer, Scirpophaga spp., e.g. Scirpophaga innotata, Scotiasegetum, Sesamia spp., e.g. Sesamia inferens, Sparganothis spp.,Spodoptera spp., e.g. Spodoptera eradiana, Spodoptera exigua, Spodopterafrugiperda, Spodoptera praefica, Stathmopoda spp., Stenoma spp.,Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora,Thaumetopoea spp., Thermesia gemmatalis, Tinea cloacella, Tineapellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella,Trichoplusia spp., e.g. Trichoplusia ni, Tryporyza incertulas, Tutaabsoluta, Virachola spp.;

from the order of the Orthoptera or Saltatoria, for example Achetadomesticus, Dichroplus spp., Gryllotalpa spp., e.g. Gryllotalpagryllotalpa, Hieroglyphus spp., Locusta spp., e.g. Locusta migratoria,Melanoplus spp., e.g. Melanoplus devastator, Paratlanticus ussuriensis,Schistocerca gregaria;

from the order of the Phthiraptera, for example Damalinia spp.,Haematopinus spp., Linognathus spp., Pediculus spp., Phylloxeravastatrix, Phthirus pubis, Trichodectes spp.;

from the order of the Psocoptera, for example Lepinotus spp., Liposcelisspp.;

from the order of the Siphonaptera, for example Ceratophyllus spp.,Ctenocephalides spp., e.g. Ctenocephalides canis, Ctenocephalides felis,Pulex irritans, Tunga penetrans, Xenopsylla cheopis;

from the order of the Thysanoptera, for example Anaphothrips obscurus,Baliothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri,Enneothrips flavens, Frankliniella spp., e.g.

Frankliniella fusca, Frankliniella occidentalis, Frankliniellaschultzei, Frankliniella tritici, Frankliniella vaccinii, Frankliniellawilliamsi, Haplothrips spp., Heliothrips spp., Hercinothrips femoralis,Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp.,Taeniothrips cardamomi, Thrips spp., e.g. Thrips palmi, Thrips tabaci;

from the order of the Zygentoma (=thysanura), e.g. Ctenolepisma spp.,Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica;

from the class of the Symphyla, for example Scutigerella spp., e.g.Scutigerella immaculata; pests from the phylum of the Mollusca, forexample from the class of the Bivalvia, e.g. Dreissena spp.; and fromthe class of the Gastropoda, for example Arion spp., e.g. Arion aterrufus, Biomphalaria spp., Bulinus spp., Deroceras spp., e.g. Deroceraslaeve, Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp.,Succinea spp.;

plant pests from the phylum of the Nematoda, i.e. phytoparasiticnematodes, in particular Aglenchus spp., e.g. Aglenchus agricola,Anguina spp., e.g. Anguina tritici, Aphelenchoides spp., e.g.Aphelenchoides arachidis, Aphelenchoides fragariae, Belonolaimus spp.,e.g. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimusnortoni, Bursaphelenchus spp., e.g. Bursaphelenchus cocophilus,Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp.,e.g. Cacopaurus pestis, Criconemella spp., e.g. Criconemella curvata,Criconemella onoensis, Criconemella ornata, Criconemella rusium,Criconemella xenoplax (=Mesocriconema xenoplax), Criconemoides spp.,e.g. Criconemoides femiae, Criconemoides onoense, Criconemoides ornatum,Ditylenchus spp., e.g. Ditylenchus dipsaci, Dolichodorus spp., Globoderaspp., e.g. Globodera pallida, Globodera rostochiensis, Helicotylenchusspp., e.g. Helicotylenchus dihystera, Hemicriconemoides spp.,Hemicycliophora spp., Heterodera spp., e.g. Heterodera avenae,Heterodera glycines, Heterodera schachtii, Hirschmaniella spp.,Hoplolaimus spp., Longidorus spp., e.g. Longidorus africanus,Meloidogyne spp., e.g. Meloidogyne chitwoodi, Meloidogyne fallax,Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp.,Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp.,Paratrichodorus spp., e.g. Paratrichodorus minor, Paratylenchus spp.,Pratylenchus spp., e.g. Pratylenchus penetrans, Pseudohalenchus spp.,Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp.,e.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp.,Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp.,e.g. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp.,e.g. Tylenchorhynchus annulatus, Tylenchulus spp., e.g. Tylenchulussemipenetrans, Xiphinema spp., e.g. Xiphinema index.

The compounds of the formula (I) can, as the case may be, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, asmicrobicides or gametocides, for example as fungicides, antimycotics,bactericides, virucides (including agents against viroids) or as agentsagainst MLO (Mycoplasma-like organisms) and RLO (Rickettsia-likeorganisms). They can, as the case may be, also be used as intermediatesor precursors for the synthesis of other active compounds.

Formulations

The present invention further relates to formulations and use formsprepared therefrom as pesticides, for example drench, drip and sprayliquors, comprising at least one compound of the formula (I).Optionally, the use forms comprise further pesticides and/or adjuvantswhich improve action, such as penetrants, e.g. vegetable oils, forexample rapeseed oil, sunflower oil, mineral oils, for example paraffinoils, alkyl esters of vegetable fatty acids, for example rapeseed oilmethyl ester or soya oil methyl ester, or alkanol alkoxylates and/orspreaders, for example alkylsiloxanes and/or salts, for example organicor inorganic ammonium or phosphonium salts, for example ammonium sulfateor diammonium hydrogenphosphate and/or retention promoters, for exampledioctyl sulfosuccinate or hydroxypropylguar polymers and/or humectants,for example glycerol and/or fertilizers, for example ammonium-,potassium- or phosphorus-containing fertilizers.

Customary formulations are, for example, water-soluble liquids (SL),emulsion concentrates (EC), emulsions in water (EW), suspensionconcentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules(GR) and capsule concentrates (CS); these and further possibleformulation types are described, for example, by Crop Life Internationaland in Pesticide Specifications, Manual on development and use of FAOand WHO specifications for pesticides, FAO Plant Production andProtection Papers—173, prepared by the FAO/WHO Joint Meeting onPesticide Specifications, 2004, ISBN: 9251048576. The formulations, inaddition to one or more compounds of the formula (I), optionallycomprise further active agrochemical ingredients.

Preference is given to formulations or use forms comprising auxiliaries,for example extenders, solvents, spontaneity promoters, carriers,emulsifiers, dispersants, frost protection agents, biocides, thickenersand/or further auxiliaries, for example adjuvants. An adjuvant in thiscontext is a component which enhances the biological effect of theformulation, without the component itself having any biological effect.Examples of adjuvants are agents which promote retention, spreading,attachment to the leaf surface or penetration.

These formulations are produced in a known manner, for example by mixingthe compounds of the formula (I) with auxiliaries, for exampleextenders, solvents and/or solid carriers and/or other auxiliaries, forexample surfactants. The formulations are produced either in suitablefacilities or else before or during application.

The auxiliaries used may be substances suitable for imparting specialproperties, such as certain physical, technical and/or biologicalproperties, to the formulation of the compounds of the formula (I), orto the use forms prepared from these formulations (for exampleready-to-use pesticides such as spray liquors or seed-dressingproducts).

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the simple and substituted amines, amides,lactams (such as N-alkylpyrrolidones) and lactones, the sulfones andsulfoxides (such as dimethyl sulfoxide).

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Useful liquid solvents areessentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulfoxide, and alsowater.

In principle, it is possible to use all suitable solvents. Examples ofsuitable solvents are aromatic hydrocarbons, for example xylene, tolueneor alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatichydrocarbons, for example chlorobenzene, chloroethylene or methylenechloride, aliphatic hydrocarbons, for example cyclohexane, paraffins,petroleum fractions, mineral and vegetable oils, alcohols, for examplemethanol, ethanol, isopropanol, butanol or glycol and their ethers andesters, ketones, for example acetone, methyl ethyl ketone, methylisobutyl ketone or cyclohexanone, strongly polar solvents, for exampledimethyl sulfoxide, and water.

In principle, it is possible to use all suitable carriers. Suitablecarriers include more particularly the following: e.g. ammonium saltsand natural, finely ground rocks, such as kaolins, aluminas, talc,chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, andsynthetic, finely ground rocks, such as highly disperse silica,aluminium oxide and natural or synthetic silicates, resins, waxes and/orsolid fertilizers. It is likewise possible to use mixtures of suchcarriers. Useful carriers for granules include: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepiolite,dolomite, and synthetic granules of inorganic and organic flours, andalso granules of organic material such as sawdust, paper, coconutshells, maize cobs and tobacco stalks.

It is also possible to use liquefied gaseous extenders or solvents.Especially suitable extenders or carriers are those which are gaseous atstandard temperature and under atmospheric pressure, for example aerosolpropellants such as halogenated hydrocarbons, and also butane, propane,nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam formers, dispersants or wettingagents having ionic or nonionic properties or mixtures of thesesurface-active substances are salts of polyacrylic acid, salts oflignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonicacid, polycondensates of ethylene oxide with fatty alcohols or withfatty acids or with fatty amines, with substituted phenols (preferablyalkylphenols or arylphenols), salts of sulfosuccinic esters, taurinederivatives (preferably alkyl taurates), phosphoric esters ofpolyethoxylated alcohols or phenols, fatty acid esters of polyols, andderivatives of the compounds containing sulfates, sulfonates andphosphates, for example alkylaryl polyglycol ethers, alkylsulfonates,alkyl sulfates, arylsulfonates, protein hydrolysates, lignosulfite wasteliquors and methylcellulose. The presence of a surfactant isadvantageous if one of the compounds of the formula (I) and/or one ofthe inert carriers is insoluble in water and if the application takesplace in water.

Further auxiliaries which may be present in the formulations and the useforms derived therefrom include dyes such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organic dyessuch as alizarin dyes, azo dyes and metal phthalocyanine dyes, andnutrients and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Additional components which may be present are stabilizers, such as coldstabilizers, preservatives, antioxidants, light stabilizers, or otheragents which improve chemical and/or physical stability. Foam generatorsor antifoams may also be present.

In addition, the formulations and the use forms derived therefrom mayalso comprise, as additional auxiliaries, stickers such ascarboxymethylcellulose and natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further auxiliaries may bemineral and vegetable oils.

It is possible if appropriate for still further auxiliaries to bepresent in the formulations and the use forms derived therefrom.Examples of such additives are fragrances, protective colloids, binders,adhesives, thickeners, thixotropic agents, penetrants, retentionpromoters, stabilizers, sequestrants, complexing agents, humectants,spreaders. In general, the compounds of the formula (I) can be combinedwith any solid or liquid additive commonly used for formulationpurposes.

Useful retention promoters include all those substances which reducedynamic surface tension, for example dioctyl sulfosuccinate, or increaseviscoelasticity, for example hydroxypropylguar polymers.

Useful penetrants in the present context are all those substances whichare typically used to improve the penetration of active agrochemicalingredients into plants. Penetrants are defined in this context by theirability to penetrate from the (generally aqueous) application liquorand/or from the spray coating into the cuticle of the plant and hence toincrease the mobility of the active compounds in the cuticle. The methoddescribed in the literature (Baur et al., 1997, Pesticide Science 51,131-152) can be used for determining this property. Examples includealcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecylethoxylate (12), fatty acid esters, for example rapeseed oil methylester or soya oil methyl ester, fatty amine alkoxylates, for exampletallowamine ethoxylate (15), or ammonium and/or phosphonium salts, forexample ammonium sulfate or diammonium hydrogenphosphate.

The formulations preferably comprise between 0.00000001% and 98% byweight of the compound of the formula (I), more preferably between 0.01%and 95% by weight of the compound of the formula (I), most preferablybetween 0.5% and 90% by weight of the compound of the formula (I), basedon the weight of the formulation.

The content of the compound of the formula (I) in the use forms preparedfrom the formulations (in particular pesticides) may vary within wideranges. The concentration of the compound of the formula (I) in the useforms may typically be between 0.00000001% and 95% by weight of thecompound of the formula (I), preferably between 0.00001% and 1% byweight, based on the weight of the use form. Application is accomplishedin a customary manner appropriate for the use forms.

Mixtures

The compounds of the formula (I) can also be used in a mixture with oneor more suitable fungicides, bactericides, acaricides, molluscicides,nematicides, insecticides, microbiological agents, beneficial organisms,herbicides, fertilizers, bird repellents, phytotonics, sterilants,safeners, semiochemicals and/or plant growth regulators, in order thus,for example, to broaden the spectrum of action, prolong the period ofaction, enhance the rate of action, prevent repellency or preventevolution of resistance. In addition, active compound combinations ofthis kind can improve plant growth and/or tolerance to abiotic factors,for example high or low temperatures, to drought or to elevated watercontent or soil salinity. It is also possible to improve flowering andfruiting performance, optimize germination capacity and rootdevelopment, facilitate harvesting and improve yields, influencematuration, improve the quality and/or the nutritional value of theharvested products, prolong storage life and/or improve theprocessibility of the harvested products.

In addition, the compounds of the formula (I) may be present in amixture with other active compounds or semiochemicals such asattractants and/or bird repellents and/or plant activators and/or growthregulators and/or fertilizers. Likewise, the compounds of the formula(I) can be used to improve plant properties, for example growth, yieldand quality of the harvested material.

In a particular embodiment according to the invention, the compounds ofthe formula (I) are present in formulations or in the use forms preparedfrom these formulations in a mixture with further compounds, preferablythose as described below.

If one of the compounds mentioned below can occur in differenttautomeric forms, these forms are also included even if not explicitlymentioned in each case. All the mixing components mentioned, as the casemay be, may also form salts with suitable bases or acids if they arecapable of doing so on the basis of their functional groups.

Insecticides/Acaricides/Nematicides

The active compounds specified here with their common names are knownand are described for example in “The Pesticide Manual”, 16th ed.,British Crop Protection Council 2012, or can be searched for on theInternet (e.g. http://www.alanwood.net/pesticides). The classificationis based on the IRAC Mode of Action Classification Scheme applicable atthe time of filing of this patent application.

(1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g.alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim,butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb,fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl,metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox,triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, e.g.acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos,chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl,coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP,dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion,ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate,heptenophos, imicyafos, isofenphos, isopropylO-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion,mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos,propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos,sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos,thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel blockers, for examplecyclodiene-organochlorines, e.g. chlordane and endosulfan orphenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

(3) Sodium channel modulators, for example pyrethroids, e.g.acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin,bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer,bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin[(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R) isomer],esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate,flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin,momfluorothrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin,pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin,tetramethrin, tetramethrin [(1R) isomer], tralomethrin and transfluthrinor DDT or methoxychlor.

(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, forexample neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran,imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine orsulfoxaflor or flupyradifurone.

(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, forexample spinosyns, e.g. spinetoram and spinosad.

(6) Glutamate-gated chloride channel (GluC1) allosteric modulators, forexample avermectins/milbemycins, e.g. abamectin, emamectin benzoate,lepimectin and milbemectin.

(7) Juvenile hormone mimetics, for example juvenile hormone analogues,e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Miscellaneous non-specific (multisite) inhibitors, for example alkylhalides, e.g. methyl bromide and other alkyl halides; or chloropicrin orsulfuryl fluoride or borax or tartar emetic or methyl isocyanategenerator, e.g. diazomet and metam.

(9) Chordotonal organ modulators, e.g. pymetrozine or flonicamide.

(10) Mite growth inhibitors, for example clofentezine, hexythiazox anddiflovidazin or etoxazole.

(11) Microbial disruptors of the insect midgut membrane, for exampleBacillus thuringiensis subspecies israelensis, Bacillus sphaericus,Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensissubspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis andB.t. plant proteins: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, Vip3A,mCry3A, Cry3Ab, Cry3Bb, Cry34 Ab1/35Ab1; or

(12) Inhibitors of mitochondrial ATP synthase, such as ATP disruptors,for example diafenthiuron or organotin compounds, e.g. azocyclotin,cyhexatin and fenbutatin oxide or propargite or tetradifon.

(13) Uncouplers of oxidative phosphorylation via disruption of theproton gradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinic acetylcholine receptor channel blockers, for examplebensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, for examplebistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

(17) Moulting disruptors (especially in the case of Diptera), forexample cyromazine.

(18) Ecdysone receptor agonists, for example chromafenozide,halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists, for example amitraz.

(20) Mitochondrial complex III electron transport inhibitors, forexample hydramethylnon or acequinocyl or fluacrypyrim.

(21) Mitochondrial complex I electron transport inhibitors, for exampleMETI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben,tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers, for example indoxacarbor metaflumizone.

(23) Inhibitors of acetyl CoA carboxylase, for example tetronic andtetramic acid derivatives, e.g. spirodiclofen, spiromesifen andspirotetramat.

(24) Mitochondrial complex IV electron transport inhibitors, for examplephosphines, e.g. aluminium phosphide, calcium phosphide, phosphine andzinc phosphide, or cyanides, calcium cyanide, potassium cyanide andsodium cyanide.

(25) Mitochondrial complex II electron transport inhibitors, for examplebeta-keto nitrile derivatives, e.g. cyenopyrafen and cyflumetofen andcarboxanilides, for example pyflubumide.

(28) Ryanodine receptor modulators, for example diamides, e.g.chlorantraniliprole, cyantraniliprole and flubendiamide,

further active compounds, for example afidopyropen, afoxolaner,azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide,bromopropylate, chinomethionat, chloroprallethrin, cryolite,cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol,epsilon metofluthrin, epsilon momfluthrin, flometoquin,fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin,flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide,fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappabifenthrin, kappa tefluthrin, lotilaner, meperfluthrin, paichongding,pyridalyl, pyrifluquinazon, pyriminostrobin, spirobudiclofen,tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole,tioxazafen, thiofluoximate, triflumezopyrim and iodomethane;additionally preparations based on Bacillus firmus (I-1582, BioNeem,Votivo), and the following compounds:1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine(known from WO2006/043635) (CAS 885026-50-6),{1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4′-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone(known from WO2003/106457) (CAS 637360-23-7),2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide(known from WO2006/003494) (CAS 872999-66-1),3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one(known from WO 2010052161) (CAS 1225292-17-0),3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethylcarbonate (known from EP 2647626) (CAS-1440516-42-6),4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine(known from WO2004/099160) (CAS 792914-58-0), PF1364 (known fromJP2010/018586) (CAS Reg. No. 1204776-60-2),N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide(known from WO2012/029672) (CAS 1363400-41-2),(3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoropropan-2-one(known from WO2013/144213) (CAS 1461743-15-6),N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide(known from WO2010/051926) (CAS 1226889-14-0),5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide(known from CN103232431) (CAS 1449220-44-3),4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide,4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)benzamideand4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide(known from WO 2013/050317 A1) (CAS 1332628-83-7),N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide,(+)—N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamideand(−)—N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide(known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1)(CAS 1477923-37-7),5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile(known from CN 101337937 A) (CAS 1105672-77-2),3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide,(Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9);N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide(known from WO 2012/034403 A1) (CAS 1268277-22-0),N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide(known from WO 2011/085575 A1) (CAS 1233882-22-8),4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine(known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide(known from CN 101715774 A) (CAS 1232543-85-9); cyclopropanecarboxylicacid 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylester (known from CN 103524422 A) (CAS 1542271-46-4);(4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylicacid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2);6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazole-3-yl]phenyl]carbamate]-α-L-mannopyranose(known from US 2014/0275503 A1) (CAS 1181213-14-8);8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 1253850-56-4),(8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(CAS 933798-27-7),(8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane(known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8) andN-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide(known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9).

Fungicides

The active compounds specified herein by their common name are known anddescribed, for example, in “Pesticide Manual” (16th Ed. British CropProtection Council) or searchable on the internet (for example:http://www.alanwood.net/pesticides).

All the mixing components mentioned in classes (1) to (15), as the casemay be, may form salts with suitable bases or acids if they are capableof doing so on the basis of their functional groups. All the fungicidalmixing components mentioned in classes (1) to (15), as the case may be,may include tautomeric forms.

1) Ergosterol biosynthesis inhibitors, for example (1.001)cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004)fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007)fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010)imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013)metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016)prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019)pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022)tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025)triticonazole, (1.026)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol(1.029)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.032)(2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.033)(2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.037)1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.038)1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.039)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.042)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.044)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.046)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.047)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.048)2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.049)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.050)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.051)2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.052)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.054)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol,(1.055)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.056)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.059)5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.060)5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.061)5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.063)N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.064)N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.065)N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.066)N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.067)N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.068)N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.069)N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.070)N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.071)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(1.072)N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.073)N′-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.074)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(1.075)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(1.076)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.077) N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.078)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.079)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.080)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.081) mefentrifluconazole, (1.082) ipfentrifluconazole.

2) Inhibitors of the respiratory chain in complex I or II, for example(2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004)carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad,(2.008) furametpyr, (2.009) isofetamid, (2.010) isopyrazam(anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimericenantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate1RS,4SR,9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate1RS,4SR,9RS and the anti-epimeric racemate 1RS,4SR,9SR), (2.014)isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam(syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimericracemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019)pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxane, (2.022)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.023)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.024)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.025)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.026)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(2.027)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.028)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.029)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.030)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.031)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.032)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.033)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine,(2.034)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.035)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.036)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.037)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.038)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.039)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.041)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.042)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.044)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.045)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(2.046)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.047)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.048)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide,(2.049)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.050)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.051)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.052)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.053)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.054)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.055)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.056)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.

3) Inhibitors of the respiratory chain in complex III, for example(3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004)coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007)dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadon, (3.010)fenamidon, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013)kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016)picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019)pyraoxystrobin, (3.020) trifloxystrobin (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,(3.022)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.024)(2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.025) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (3.026)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.027)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,(3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.029) methyl{5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate.

4) Mitosis and cell division inhibitors, for example (4.001)carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004)fluopicolid, (4.005) pencycuron, (4.006) thiabendazole, (4.007)thiophanate-methyl, (4.008) zoxamide, (4.009)3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(4.011)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine,(4.012)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.013)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.014)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.015)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.016)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.017)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.018)4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.019)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.020)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.021)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.022)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(4.023)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.024)N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.025)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

5) Compounds having capacity for multisite activity, for example (5.001)Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004)chlorthalonil, (5.005) copper hydroxide, (5.006) copper naphthenate,(5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+)sulfate, (5.010) dithianon, (5.011) dodin, (5.012) folpet, (5.013)mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017)copper oxine, (5.018) propineb, (5.019) sulfur and sulfur preparationsincluding calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022)ziram, (5.023)6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3′,4′:5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

6) Compounds capable of triggering host defence, for example (6.001)acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004)tiadinil.

7) Amino acid and/or protein biosynthesis inhibitors, for example(7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycinhydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil,(7.006)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

(8) ATP production inhibitors, for example (8.001) silthiofam.

9) Cell wall synthesis inhibitors, for example (9.001) benthiavalicarb,(9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005)mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(9.009)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

10) Lipid and membrane synthesis inhibitors, for example (10.001)propamocarb, (10.002) propamocarb hydrochloride, (10.003)tolclofos-methyl.

11) Melanin biosynthesis inhibitors, for example (11.001) tricyclazole,(11.002) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl,(12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004)metalaxyl-M (mefenoxam).

13) Signal transduction inhibitors, for example (13.001) fludioxonil,(13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005)quinoxyfen, (13.006) vinclozolin.

14) Compounds that can act as uncouplers, for example (14.001)fluazinam, (14.002) meptyldinocap.

15) Further compounds, for example (15.001) abscisic acid, (15.002)benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone,(15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid,(15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil,(15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014)fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon,(15.017) mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021)oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024)pentachlorophenol and salts, (15.025) phosphonic acid and salts thereof,(15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone)(15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide,(15.031)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.032) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034)2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.035)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.036)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.037)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.038)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.040)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.041)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol,(15.042)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol,(15.043)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.044)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate, (15.045) 2-phenylphenol and salts thereof, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.047)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.049)4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050)5-amino-1,3,4-thiadiazole-2-thiol, (15.051)5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene 2-sulfonohydrazide,(15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,(15.055) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057)phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate,(15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061)tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.062)5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one.

Biological Pesticides as Mixing Components

The compounds of the formula (I) can be combined with biologicalpesticides.

Biological pesticides especially include bacteria, fungi, yeasts, plantextracts and products formed by microorganisms, including proteins andsecondary metabolites.

Biological pesticides include bacteria such as spore-forming bacteria,root-colonizing bacteria and bacteria which act as biologicalinsecticides, fungicides or nematicides.

Examples of such bacteria which are used or can be used as biologicalpesticides are:

Bacillus amyloliquefaciens, strain FZB42 (DSM 231179), or Bacilluscereus, especially B. cereus strain CNCM I-1562 or Bacillus firmus,strain I-1582 (Accession number CNCM I-1582) or Bacillus pumilus,especially strain GB34 (Accession No. ATCC 700814) and strain QST2808(Accession No. NRRL B-30087), or Bacillus subtilis, especially strainGBO03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713(Accession No. NRRL B-21661) or Bacillus subtilis strain OST 30002(Accession No. NRRL B-50421), Bacillus thuringiensis, especially B.thuringiensis subspecies israelensis (serotype H-14), strain AM65-52(Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai,especially strain ABTS-1857 (SD-1372), or B. thuringiensis subsp.kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulusreniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomycesmicroflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomycesgalbus strain AQ 6047 (Accession Number NRRL 30232).

Examples of fungi and yeasts which are used or can be used as biologicalpesticides are:

Beauveria bassiana, in particular strain ATCC 74040, Coniothyriumminitans, in particular strain CON/M/91-8 (Accession No. DSM-9660),Lecanicillium spp., in particular strain HRO LEC 12, Lecanicilliumlecanii (formerly known as Verticillium lecanii), in particular strainKV01, Metarhizium anisopliae, in particular strain F52 (DSM3884/ATCC90448), Metschnikowia fructicola, in particular strain NRRL Y-30752,Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particularstrain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874),Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL89/030550), Talaromyces flavus, in particular strain V117b, Trichodermaatroviride, in particular strain SC1 (Accession Number CBS 122089),Trichoderma harzianum, in particular T. harzianum rifai T39 (accessionnumber CNCM I-952).

Examples of viruses which are used or can be used as biologicalpesticides are:

Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydiapomonella (codling moth) granulosis virus (GV), Helicoverpa armigera(cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua(beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV,Spodoptera littoralis (African cotton leafworm) NPV.

Also included are bacteria and fungi which are added as ‘inoculant’ toplants or plant parts or plant organs and which, by virtue of theirparticular properties, promote plant growth and plant health.

Examples Include:

Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp.,Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especiallyBurkholderia cepacia (formerly known as Pseudomonas cepacia), Gigasporaspp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillusbuchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp.,Rhizobium spp., especially Rhizobium trifolii, Rhizopogon spp.,Scleroderma spp., Suillus spp., Streptomyces spp.

Examples of plant extracts and products formed by microorganisms,including proteins and secondary metabolites, which are used or can beused as biological pesticides are:

Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassianigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin,Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune aza,Fungastop, Heads Up (Chenopodium quinoa saponin extract),pyrethrum/pyrethrins, Quassia amara, Quercus, Quillaja, Regalia,“Requiem™ Insecticide”, rotenone, Ryania/ryanodine, Symphytumofficinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulummajus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract,especially oilseed rape powder or mustard powder.

Safener as Mixing Components

The compounds of the formula (I) can be combined with safeners, forexample benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide,dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim,furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalicanhydride, oxabetrinil,2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS52836-31-4).

Plants and Plant Parts

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and populationsof plants, such as desirable and undesirable wild plants or crop plants(including naturally occurring crop plants), for example cereals (wheat,rice, triticale, barley, rye, oats), maize, soya beans, potatoes, sugarbeet, sugar cane, tomatoes, bell peppers, cucumbers, melons, carrots,water melons, onions, lettuce, spinach, leeks, beans, Brassica oleracea(e.g. cabbage) and other vegetable species, cotton, tobacco, oilseedrape, and also fruit plants (the fruits being apples, pears, citrusfruits and grapes). Crop plants may be plants which can be obtained byconventional breeding and optimization methods or by biotechnologicaland genetic engineering methods or combinations of these methods,including the transgenic plants and including the plant cultivars whichare protectable or non-protectable by plant breeders' rights. Plantsshall be understood to mean all development stages such as seed,seedlings, young (immature) plants, up to and including mature plants.Plant parts shall be understood to mean all parts and organs of theplants above and below ground, such as shoot, leaf, flower and root,examples given being leaves, needles, stalks, stems, flowers, fruitbodies, fruits and seeds, and also roots, tubers and rhizomes. Plantparts also include harvested plants or harvested plant parts andvegetative and generative propagation material, for example cuttings,tubers, rhizomes, slips and seeds.

The inventive treatment of the plants and parts of plants with thecompounds of the formula (I) is effected directly or by allowing thecompounds to act on the surroundings, the habitat or the storage spacethereof by the customary treatment methods, for example by dipping,spraying, evaporating, fogging, scattering, painting on, injecting, and,in the case of propagation material, especially in the case of seeds,also by applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts in accordance with the invention. In a preferred embodiment, wildplant species and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof are treated. Theterm “parts” or “parts of plants” or “plant parts” has been explainedabove. Particular preference is given in accordance with the inventionto treating plants of the respective commercially customary plantcultivars or those that are in use. Plant cultivars are understood tomean plants having new properties (“traits”) and which have beenobtained by conventional breeding, by mutagenesis or by recombinant DNAtechniques. They may be cultivars, varieties, biotypes or genotypes.

Transgenic Plants, Seed Treatment and Integration Events

The preferred transgenic plants or plant cultivars (those obtained bygenetic engineering) which are to be treated in accordance with theinvention include all plants which, through the genetic modification,received genetic material which imparts particular advantageous usefulproperties (“traits”) to these plants. Examples of such properties arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to levels of water or soil salinity,enhanced flowering performance, easier harvesting, accelerated ripening,higher harvest yields, higher quality and/or higher nutritional value ofthe harvested products, better capability for storage and/orprocessability of the harvested products. Further and particularlyemphasized examples of such properties are increased resistance of theplants to animal and microbial pests, such as insects, arachnids,nematodes, mites, slugs and snails, owing, for example, to toxins formedin the plants, in particular those formed in the plants by the geneticmaterial from Bacillus thuringiensis (for example by the genes CryIA(a),CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb andCryIF and also combinations thereof), and also increased resistance ofthe plants to phytopathogenic fungi, bacteria and/or viruses caused, forexample, by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and correspondingly expressed proteinsand toxins, and also increased tolerance of the plants to certain activeherbicidal compounds, for example imidazolinones, sulfonylureas,glyphosate or phosphinothricin (for example the “PAT” gene). The geneswhich impart the desired properties (“traits”) in question may also bepresent in combinations with one another in the transgenic plants.Examples of transgenic plants mentioned include the important cropplants, such as cereals (wheat, rice, triticale, barley, rye, oats),maize, soya beans, potatoes, sugar beet, sugar cane, tomatoes, peas andother types of vegetable, cotton, tobacco, oilseed rape and also fruitplants (the fruits being apples, pears, citrus fruits and grapevines),particular emphasis being given to maize, soya beans, wheat, rice,potatoes, cotton, sugar cane, tobacco and oilseed rape. Properties(“traits”) which are particularly emphasized are the increasedresistance of the plants to insects, arachnids, nematodes and slugs andsnails.

Crop Protection—Types of Treatment

The plants and plant parts are treated with the compounds of the formula(I) directly or by action on their surroundings, habitat or storagespace using customary treatment methods, for example by dipping,spraying, atomizing, irrigating, evaporating, dusting, fogging,broadcasting, foaming, painting, spreading-on, injecting, watering(drenching), drip irrigating and, in the case of propagation material,in particular in the case of seed, additionally by dry seed treatment,liquid seed treatment, slurry treatment, by incrusting, by coating withone or more coats, etc. It is furthermore possible to apply thecompounds of the formula (I) by the ultra-low volume method or to injectthe application form or the compound of the formula (I) itself into thesoil.

A preferred direct treatment of the plants is foliar application,meaning that the compounds of the formula (I) are applied to thefoliage, in which case the treatment frequency and the application rateshould be adjusted according to the level of infestation with the pestin question.

In the case of systemically active compounds, the compounds of theformula (I) also access the plants via the root system. The plants arethen treated by the action of the compounds of the formula (I) on thehabitat of the plant. This can be accomplished, for example, bydrenching, or by mixing into the soil or the nutrient solution, meaningthat the locus of the plant (e.g. soil or hydroponic systems) isimpregnated with a liquid form of the compounds of the formula (I), orby soil application, meaning that the compounds of the formula (I)according to the invention are introduced in solid form (e.g. in theform of granules) into the locus of the plants. In the case of paddyrice crops, this can also be accomplished by metering the compound ofthe formula (I) in a solid application form (for example as granules)into a flooded paddy field.

Seed Treatment

The control of animal pests by the treatment of the seed of plants haslong been known and is the subject of constant improvements.Nevertheless, the treatment of seed entails a series of problems whichcannot always be solved in a satisfactory manner. Thus, it is desirableto develop methods for protecting the seed and the germinating plantwhich dispense with, or at least reduce considerably, the additionalapplication of pesticides during storage, after sowing or afteremergence of the plants. It is additionally desirable to optimize theamount of active compound used so as to provide optimum protection forthe seed and the germinating plant from attack by animal pests, butwithout damage to the plant itself by the active compound used. Inparticular, methods for the treatment of seed should also take accountof the intrinsic insecticidal or nematicidal properties ofpest-resistant or -tolerant transgenic plants in order to achieveoptimal protection of the seed and also the germinating plant with aminimum expenditure on pesticides.

The present invention therefore in particular also relates to a methodfor the protection of seed and germinating plants from attack by pests,by treating the seed with one of the compounds of the formula (I). Themethod according to the invention for protecting seed and germinatingplants against attack by pests further comprises a method in which theseed is treated simultaneously in one operation or sequentially with acompound of the formula (I) and a mixing component. It further alsocomprises a method where the seed is treated at different times with acompound of the formula (I) and a mixing component.

The invention also relates to the use of the compounds of the formula(I) for the treatment of seed for protecting the seed and the resultingplant from animal pests.

The invention further relates to seed which has been treated with acompound of the formula (I) according to the invention for protectionfrom animal pests. The invention also relates to seed which has beentreated simultaneously with a compound of the formula (I) and a mixingcomponent. The invention further relates to seed which has been treatedat different times with a compound of the formula (I) and a mixingcomponent. In the case of seed which has been treated at different timeswith a compound of the formula (I) and a mixing component, theindividual substances may be present on the seed in different layers. Inthis case, the layers comprising a compound of the formula (I) andmixing components may optionally be separated by an intermediate layer.The invention also relates to seed in which a compound of the formula(I) and a mixing component have been applied as part of a coating or asa further layer or further layers in addition to a coating.

The invention further relates to seed which, after the treatment with acompound of the formula (I), is subjected to a film-coating process toprevent dust abrasion on the seed.

One of the advantages that occur when a compound of the formula (I) actssystemically is that the treatment of the seed protects not only theseed itself but also the plants resulting therefrom, after emergence,from animal pests. In this way, the immediate treatment of the crop atthe time of sowing or shortly thereafter can be dispensed with.

A further advantage is that the treatment of the seed with a compound ofthe formula (I) can enhance germination and emergence of the treatedseed.

It is likewise considered to be advantageous that compounds of theformula (I) can especially also be used for transgenic seed.

Furthermore, compounds of the formula (I) can be employed in combinationwith compositions of signalling technology, leading to bettercolonization by symbionts such as, for example, rhizobia, mycorrhizaeand/or endophytic bacteria or fungi, and/or to optimized nitrogenfixation.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in the greenhouse, inforests or in horticulture. More particularly, this is the seed ofcereals (for example wheat, barley, rye, millet and oats), maize,cotton, soya beans, rice, potatoes, sunflowers, coffee, tobacco, canola,oilseed rape, beets (for example sugar beets and fodder beets), peanuts,vegetables (for example tomatoes, cucumbers, beans, cruciferousvegetables, onions and lettuce), fruit plants, lawns and ornamentalplants. Of particular significance is the treatment of the seed ofcereals (such as wheat, barley, rye and oats), maize, soya beans,cotton, canola, oilseed rape, vegetables and rice.

As already mentioned above, the treatment of transgenic seed with acompound of the formula (I) is also of particular importance. Thisinvolves the seed of plants which generally contain at least oneheterologous gene which controls the expression of a polypeptide havinginsecticidal and/or nematicidal properties in particular. Theheterologous genes in transgenic seed may originate from microorganismssuch as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. The present invention isparticularly suitable for treatment of transgenic seed which comprisesat least one heterologous gene originating from Bacillus sp. Theheterologous gene is more preferably derived from Bacillusthuringiensis.

In the context of the present invention, the compound of the formula (I)is applied to the seed. The seed is preferably treated in a state inwhich it is sufficiently stable for no damage to occur in the course oftreatment. In general, the seed can be treated at any time betweenharvest and sowing. It is customary to use seed which has been separatedfrom the plant and freed from cobs, shells, stalks, coats, hairs or theflesh of the fruits. For example, it is possible to use seed which hasbeen harvested, cleaned and dried down to a moisture content whichallows storage. Alternatively, it is also possible to use seed which,after drying, has been treated with, for example, water and then driedagain, for example priming. In the case of rice seed, it is alsopossible to use seed which has been soaked, for example in water, untilit reaches a certain stage of the rice embryo (“pigeon breast stage”)which results in stimulation of germination and more uniform emergence.

When treating the seed, care must generally be taken that the amount ofthe compound of the formula (I) applied to the seed and/or the amount offurther additives is chosen in such a way that the germination of theseed is not adversely affected, or that the resulting plant is notdamaged. This has to be ensured particularly in the case of activecompounds which can exhibit phytotoxic effects at certain applicationrates.

In general, the compounds of the formula (I) are applied to the seed inthe form of a suitable formulation. Suitable formulations and processesfor seed treatment are known to the person skilled in the art.

The compounds of the formula (I) can be converted to the customaryseed-dressing formulations, such as solutions, emulsions, suspensions,powders, foams, slurries or other coating compositions for seed, andalso ULV formulations.

These formulations are prepared in a known manner, by mixing thecompounds of the formula (I) with customary additives, for examplecustomary extenders and solvents or diluents, dyes, wetting agents,dispersants, emulsifiers, antifoams, preservatives, secondarythickeners, adhesives, gibberellins, and also water.

Dyes which may be present in the seed-dressing formulations usable inaccordance with the invention are all dyes which are customary for suchpurposes. It is possible to use either pigments, which are sparinglysoluble in water, or dyes, which are soluble in water. Examples includethe dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I.Solvent Red 1.

Useful wetting agents which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are customary for the formulation ofactive agrochemical ingredients. Usable with preference are alkylnaphthalenesulfonates, such as diisopropyl or diisobutylnaphthalenesulfonates.

Suitable dispersants and/or emulsifiers which may be present in theseed-dressing formulations usable in accordance with the invention areall nonionic, anionic and cationic dispersants customary for theformulation of active agrochemical ingredients. Nonionic or anionicdispersants or mixtures of nonionic or anionic dispersants can be usedwith preference. Suitable nonionic dispersants especially includeethylene oxide/propylene oxide block polymers, alkylphenol polyglycolethers and tristyrylphenol polyglycol ethers, and the phosphated orsulfated derivatives thereof. Suitable anionic dispersants areespecially lignosulfonates, polyacrylic acid salts andarylsulfonate-formaldehyde condensates.

Antifoams which may be present in the seed-dressing formulations usablein accordance with the invention are all foam-inhibiting substancescustomary for the formulation of active agrochemical ingredients.Silicone antifoams and magnesium stearate can be used with preference.

Preservatives which may be present in the seed-dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed-dressingformulations usable in accordance with the invention are all substanceswhich can be used for such purposes in agrochemical compositions.

Preferred examples include cellulose derivatives, acrylic acidderivatives, xanthan, modified clays and finely divided silica.

Useful stickers which may be present in the seed-dressing formulationsusable in accordance with the invention are all customary binders usablein seed-dressing products. Preferred examples includepolyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Gibberellins which may be present in the seed-dressing formulationsusable in accordance with the invention are preferably the gibberellinsA1, A3 (=gibberellic acid), A4 and A7; particular preference is given tousing gibberellic acid. The gibberellins are known (cf. R. Wegler“Chemie der Pflanzenschutz-und Schädlingsbekampfungsmittel”, vol. 2,Springer Verlag, 1970, pp. 401-412).

The seed-dressing formulations usable in accordance with the inventioncan be used to treat a wide variety of different kinds of seed, eitherdirectly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats and triticale, and also the seed of maize, rice, oilseed rape,peas, beans, cotton, sunflowers, soya beans and beets, or else a widevariety of different vegetable seed. The seed-dressing formulationsusable in accordance with the invention, or the dilute use formsthereof, can also be used to dress seed of transgenic plants.

For the treatment of seed with the seed-dressing formulations usable inaccordance with the invention, or the use forms prepared therefromthrough the addition of water, all mixing units usable customarily forthe seed dressing are useful. Specifically, the procedure in seeddressing is to place the seed into a mixer in batchwise or continuousoperation, to add the particular desired amount of seed-dressingformulations, either as such or after prior dilution with water, and tomix until the formulation is distributed homogeneously on the seed. Ifappropriate, this is followed by a drying operation.

The application rate of the seed dressing formulations usable inaccordance with the invention can be varied within a relatively widerange. It is guided by the particular content of the compounds of theformula (I) in the formulations and by the seed. The application ratesof the compound of the formula (I) are generally between 0.001 and 50 gper kilogram of seed, preferably between 0.01 and 15 g per kilogram ofseed.

Animal Health

In the animal health field, i.e. the field of veterinary medicine, thecompounds of the formula (I) are active against animal parasites, inparticular ectoparasites or endoparasites. The term “endoparasite”includes especially helminths and protozoa, such as coccidia.Ectoparasites are typically and preferably arthropods, especiallyinsects or acarids.

In the field of veterinary medicine, the compounds of the formula (I)having favourable endotherm toxicity are suitable for controllingparasites which occur in animal breeding and animal husbandry inlivestock, breeding animals, zoo animals, laboratory animals,experimental animals and domestic animals. They are active against allor specific stages of development of the parasites.

Agricultural livestock include, for example, mammals, such as sheep,goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deerand especially cattle and pigs; or poultry such as turkeys, ducks, geeseand especially chickens; or fish or crustaceans, for example inaquaculture; or, as the case may be, insects such as bees.

Domestic animals include, for example, mammals, such as hamsters, guineapigs, rats, mice, chinchillas, ferrets, and particularly dogs, cats,caged birds; reptiles, amphibians or aquarium fish.

In a specific embodiment, the compounds of the formula (I) areadministered to mammals.

In another specific embodiment, the compounds of the formula (I) areadministered to birds, namely caged birds or particularly poultry.

Use of the compounds of the formula (I) for the control of animalparasites is intended to reduce or prevent illness, cases of death andreductions in performance (in the case of meat, milk, wool, hides, eggs,honey and the like), such that more economical and simpler animalhusbandry is enabled and better animal well-being is achievable.

In relation to the field of animal health, the term “control” or“controlling” in the present context means that the compounds of theformula (I) are effective in reducing the incidence of the particularparasite in an animal infected with such parasites to an innocuousdegree. More specifically, “controlling” in the present context meansthat the compounds of the formula (I) kill the respective parasite,inhibit its growth, or inhibit its proliferation.

The arthropods include, for example, but are not limited to, from theorder of Anoplurida, for example, Haematopinus spp., Linognathus spp.,Pediculus spp., Phtirus spp. and Solenopotes spp.;

from the order of Mallophagida and the suborders Amblycerina andIschnocerina, for example, Bovicola spp., Damalina spp., Felicola spp.;Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp.,Trinoton spp., Werneckiella spp;

from the order of Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Atylotus spp.,Braula spp., Calliphora spp., Chrysomyia spp., Chrysops spp., Culexspp., Culicoides spp., Eusimulium spp., Fannia spp., Gasterophilus spp.,Glossina spp., Haematobia spp., Haematopota spp., Hippobosca spp.,Hybomitra spp., Hydrotaea spp., Hypoderma spp., Lipoptena spp., Luciliaspp., Lutzomyia spp., Melophagus spp., Morellia spp., Musca spp.,Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp.,Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanusspp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp.;

from the order of Siphonapterida, for example, Ceratophyllus spp.,Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp.;

from the order of heteropterida, for example, Cimex spp., Panstrongylusspp., Rhodnius spp., Triatoma spp.; and also nuisance and hygiene pestsfrom the order Blattarida.

In addition, in the case of the arthropods, mention should be made byway of example, without limitation, of the following Acari:

from the subclass of Acari (Acarina) and the order of Metastigmata, forexample from the family of Argasidae such as Argas spp., Omithodorusspp., Otobius spp., from the family of Ixodidae such as Amblyomma spp.,Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ixodes spp.,Rhipicephalus (Boophilus) spp., Rhipicephalus spp. (the original genusof multi-host ticks); from the order of Mesostigmata such as Dermanyssusspp., Ornithonyssus spp., Pneumonyssus spp., Raillietia spp.,Sternostoma spp., Tropilaelaps spp., Varroa spp.; from the order of theActinedida (Prostigmata), for example, Acarapis spp., Cheyletiella spp.,Demodex spp., Listrophorus spp., Myobia spp., Neotrombicula spp.,Omithocheyletia spp., Psorergates spp., Trombicula spp.; and from theorder of the Acaridida (Astigmata), for example, Acarus spp.,Caloglyphus spp., Chorioptes spp., Cytodites spp., Hypodectes spp.,Knemidocoptes spp., Laminosioptes spp., Notoedres spp., Otodectes spp.,Psoroptes spp., Pterolichus spp., Sarcoptes spp., Trixacarus spp.,Tyrophagus spp.

Examples of parasitic protozoa include, but are not limited to:

Mastigophora (flagellata), such as:

Metamonada: from the order of Diplomonadida, for example, Giardia spp.,Spironucleus spp.

Parabasala: from the order of Trichomonadida, for example, Histomonasspp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp.,Tritrichomonas spp.

Euglenozoa: from the order of Trypanosomatida, for example, Leishmaniaspp., Trypanosoma spp.

Sarcomastigophora (rhizopoda) such as Entamoebidae, for example,Entamoeba spp., Centramoebidae, for example Acanthamoeba sp.,Euamoebidae, e.g. Hartmanella sp.

Alveolata such as Apicomplexa (Sporozoa): e.g. Cryptosporidium spp.;from the order of Eimeriida, for example, Besnoitia spp., Cystoisosporaspp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp.,Sarcocystis spp., Toxoplasma spp.; from the order of Adeleida, forexample, Hepatozoon spp., Klossiella spp.; from the order ofHaemosporida, for example, Leucocytozoon spp., Plasmodium spp.; from theorder of Piroplasmida, for example, Babesia spp., Ciliophora spp.,Echinozoon spp., Theileria spp.; from the order of Vesibuliferida, forexample, Balantidium spp., Buxtonella spp.

Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidiumspp., Nosema spp., and also, for example, Myxozoa spp.

The helminths that are pathogenic to humans or animals include, forexample, Acanthocephala, nematodes, pentastoma and Platyhelminthes (e.g.Monogenea, cestodes and Trematodes).

Illustrative helminths include, but are not limited to:

Monogenea: e.g. Dactylogyrus spp., Gyrodactylus spp., Microbothriumspp., Polystoma spp., Troglecephalus spp.;

Cestodes: from the order of Pseudophyllidea, for example: Bothridiumspp., Diphyllobothrium spp., Diplogonoporus spp., Ichthyobothrium spp.,Ligula spp., Schistocephalus spp., Spirometra spp.

From the order of Cyclophyllida, for example: Andyra spp., Anoplocephalaspp., Avitellina spp., Bertiella spp., Cittotaenia spp., Davainea spp.,Diorchis spp., Diplopylidium spp., Dipylidium spp., Echinococcus spp.,Echinocotyle spp., Echinolepis spp., Hydatigera spp., Hymenolepis spp.,Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephalaspp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp.,Thysanosoma spp.

Trematodes: from the class of Digenea, for example: Austrobilharziaspp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchisspp. Collyriclum spp., Cotylophoron spp., Cyclocoelum spp., Dicrocoeliumspp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp.,Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp.,Fasciolopsis spp., Fischoederius spp., Gastrothylacus spp.,Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeumspp., Leucochloridium spp., Metagonimus spp., Metorchis spp.,Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Omithobilharziaspp., Paragonimus spp., Paramphistomum spp., Plagiorchis spp.,Posthodiplostomum spp., Prosthogonimus spp., Schistosoma spp.,Trichobilharzia spp., Troglotrema spp., Typhlocoelum spp.

Nematodes: from the order of Trichinellida, for example: Capillariaspp., Trichinella spp., Trichomosoides spp., Trichuris spp.

From the order of Tylenchida, for example: Micronema spp.,Parastrangyloides spp., Strongyloides spp.

From the order of Rhabditina, for example: Aelurostrongylus spp.,Amidostomum spp., Ancylostoma spp., Angiostrongylus spp., Bronchonemaspp., Bunostomum spp., Chabertia spp., Cooperia spp., Cooperioides spp.,Crenosoma spp., Cyathostomum spp., Cyclococercus spp., Cyclodontostomumspp., Cylicocyclus spp., Cylicostephanus spp., Cylindropharynx spp.,Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroidesspp., Globocephalus spp., Graphidium spp., Gyalocephalus spp.,Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagiaspp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirusspp., Neostrongylus spp., Nippostrongylus spp., Obeliscoides spp.,Oesophagodontus spp., Oesophagostomum spp., Ollulanus spp.;Omithostrongylus spp., Oslerus spp., Ostertagia spp., Paracooperia spp.,Paracrenosoma spp., Parafilaroides spp., Parelaphostrongylus spp.,Pneumocaulus spp., Pneumostrongylus spp., Poteriostomum spp.,Protostrongylus spp., Spicocaulus spp., Stephanurus spp., Strongylusspp., Syngamus spp., Teladorsagia spp., Trichonema spp.,Trichostrongylus spp., Triodontophorus spp., Troglostrongylus spp.,Uncinaria spp.

From the order of Spirurida, for example: Acanthocheilonema spp.,Anisakis spp., Ascaridia spp.; Ascaris spp., Ascarops spp., Aspiculurisspp., Baylisascaris spp., Brugia spp., Cercopithifilaria spp.,Crassicauda spp., Dipetalonema spp., Dirofilaria spp., Dracunculus spp.;Draschia spp., Enterobius spp., Filaria spp., Gnathostoma spp.,Gongylonema spp., Habronema spp., Heterakis spp.; Litomosoides spp., Loaspp., Onchocerca spp., Oxyuris spp., Parabronema spp., Parafilaria spp.,Parascaris spp., Passalurus spp., Physaloptera spp., Probstmayria spp.,Pseudofilaria spp., Setaria spp., Skjrabinema spp., Spirocerca spp.,Stephanofilaria spp., Strongyluris spp., Syphacia spp., Thelazia spp.,Toxascaris spp., Toxocara spp., Wuchereria spp.

Acanthocephala: from the order of Oligacanthorhynchida, for example:Macracanthorhynchus spp., Prosthenorchis spp.; from the order ofMoniliformida, for example: Moniliformis spp.

From the order of Polymorphida, for example: Filicollis spp.; from theorder of Echinorhynchida, for example Acanthocephalus spp.,Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: from the order of Porocephalida, for example, Linguatulaspp.

In the veterinary field and in animal husbandry, the compounds of theformula (I) are administered by methods generally known in the art, suchas via the enteral, parenteral, dermal or nasal route in the form ofsuitable preparations. Administration may be prophylactic, metaphylacticor therapeutic.

Thus, one embodiment of the present invention relates to the compoundsof the formula (I) for use as a medicament.

A further aspect relates to the compounds of the formula (I) for use asan antiendoparasitic agent.

A further specific aspect of the invention relates to the compounds ofthe formula (I) for use as an antithelminthic agent, especially for useas a nematicide, platyhelminthicide, acanthocephalicide orpentastomicide.

A further specific aspect of the invention relates to the compounds ofthe formula (I) for use as an antiprotozoic agent.

A further aspect relates to the compounds of the formula (I) for use asan antiectoparasitic agent, especially an arthropodicide, veryparticularly an insecticide or an acaricide.

Further aspects of the invention are veterinary medicine formulationscomprising an effective amount of at least one compound of the formula(I) and at least one of the following: a pharmaceutically acceptableexcipient (e.g. solid or liquid diluents), a pharmaceutically acceptableauxiliary (e.g. surfactants), especially a pharmaceutically acceptableexcipient used conventionally in veterinary medicine formulations and/ora pharmaceutically acceptable auxiliary conventionally used inveterinary medicine formulations.

A related aspect of the invention is a method for production of aveterinary medicine formulation as described here, which comprises thestep of mixing at least one compound of the formula (I) withpharmaceutically acceptable excipients and/or auxiliaries, especiallywith pharmaceutically acceptable excipients used conventionally inveterinary medicine formulations and/or auxiliaries used conventionallyin veterinary medicine formulations.

Another specific aspect of the invention is veterinary medicineformulations selected from the group of ectoparasiticidal andendoparasiticidal formulations, especially selected from the group ofanthelmintic, antiprotozoic and arthropodicidal formulations, veryparticularly selected from the group of nematicidal,platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidaland acaricidal formulations, according to the aspects mentioned, andmethods for production thereof.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof an effective amount of a compound of the formula (I) in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to a method for treatment of a parasiticinfection, especially an infection caused by a parasite selected fromthe group of the ectoparasites and endoparasites mentioned here, by useof a veterinary medicine formulation as defined here in an animal,especially a nonhuman animal, having a need therefor.

Another aspect relates to the use of the compounds of the formula (I) inthe treatment of a parasite infection, especially an infection caused bya parasite selected from the group of the ectoparasites andendoparasites mentioned here, in an animal, especially a nonhumananimal.

In the present context of animal health or veterinary medicine, the term“treatment” includes prophylactic, metaphylactic and therapeutictreatment.

In a particular embodiment, in this way, mixtures of at least onecompound of the formula (I) with other active compounds, especially withendo- and ectoparasiticides, are provided for the field of veterinarymedicine.

In the field of animal health, “mixture” means not just that two (ormore) different active compounds are formulated in a common formulationand are correspondingly employed together, but also relates to productscomprising formulations separated for each active compound. Accordingly,when more than two active compounds are to be employed, all activecompounds can be formulated in a common formulation or all activecompounds can be formulated in separate formulations; likewiseconceivable are mixed forms in which some of the active compounds areformulated together and some of the active compounds are formulatedseparately. Separate formulations allow the separate or successiveapplication of the active compounds in question.

The active compounds specified here by their “common names” are knownand are described, for example, in the “Pesticide Manual” (see above) orcan be searched for on the Internet (e.g.: alanwood.netipesticides).

Illustrative active compounds from the group of the ectoparasiticides asmixing components include, without any intention that this shouldconstitute a restriction, the insecticides and acaricides listed indetail above. Further usable active compounds are listed below inaccordance with the abovementioned classification based on the currentIRAC Mode of Action Classification Scheme: (1) acetylcholinesterase(AChE) inhibitors; (2) GABA-gated chloride channel blockers; (3) sodiumchannel modulators; (4) nicotinic acetylcholine receptor (nAChR)competitive modulators; (5) nicotinic acetylcholine receptor (nAChR)allosteric modulators; (6) glutamate-gated chloride channel (GluCl)allosteric modulators; (7) juvenile hormone mimetics; (8) miscellaneousnon-specific (multi-site) inhibitors; (9) chordotonal organ modulators;(10) mite growth inhibitors; (12) inhibitors of mitochondrial ATPsynthase, such as ATP disruptors; (13) uncouplers of oxidativephosphorylation via disruption of the proton gradient; (14) nicotinicacetylcholine receptor channel blockers; (15) inhibitors of chitinbiosynthesis, type 0; (16) inhibitors of chitin biosynthesis, type 1;(17) moulting disruptors (especially in Diptera); (18) ecdysone receptoragonists; (19) octopamine receptor agonists; (21) mitochondrial complexI electron transport inhibitors; (25) mitochondrial complex II electrontransport inhibitors; (20) mitochondrial complex III electron transportinhibitors; (22) voltage-dependent sodium channel blockers; (23)inhibitors of acetyl CoA carboxylase; (28) ryanodine receptormodulators; active compounds having unknown or non-specific mechanismsof action, e.g. fentrifanil, fenoxacrim, cycloprene, chlorobenzilate,chlordimeform, flubenzimin, dicyclanil, amidoflumet, quinomethionat,triarathene, clothiazoben, tetrasul, potassium oleate, petroleum,metoxadiazone, gossyplur, flutenzine, brompropylate, cryolite;

compounds from other classes, for example butacarb, dimetilan,cloethocarb, phosphocarb, pirimiphos(-ethyl), parathion(-ethyl),methacrifos, isopropyl o-salicylate, trichlorfon, sulprofos, propaphos,sebufos, pyridathion, prothoate, dichlofenthion, demeton-S-methylsulfone, isazofos, cyanofenphos, dialifos, carbophenothion, autathiofos,aromfenvinfos(-methyl), azinphos(-ethyl), chlorpyrifos(-ethyl),fosmethilan, iodofenphos, dioxabenzofos, formothion, fonofos,flupyrazofos, fensulfothion, etrimfos;

organochlorine compounds, for example camphechlor, lindane, heptachlor;or phenylpyrazoles, e.g. acetoprole, pyrafluprole, pyriprole,vaniliprole, sisapronil; or isoxazolines, e.g. sarolaner, afoxolaner,lotilaner, fluralaner;

pyrethroids, e.g. (cis-, trans-)metofluthrin, profluthrin, flufenprox,flubrocythrinate, fubfenprox, fenfluthrin, protrifenbut, pyresmethrin,RU15525, terallethrin, cis-resmethrin, heptafluthrin, bioethanomethrin,biopermethrin, fenpyrithrin, cis-cypermethrin, cis-permethrin,clocythrin, cyhalothrin (lambda-), chlovaporthrin, or halogenatedhydrocarbon compounds (HCHs),

neonicotinoids, e.g. nithiazine

dicloromezotiaz, triflumezopyrim

macrocyclic lactones, e.g. nemadectin, ivermectin, latidectin,moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate;milbemycin oxime

triprene, epofenonane, diofenolan;

biologicals, hormones or pheromones, for example natural products, e.g.thuringiensin, codlemone or neem components

dinitrophenols, e.g. dinocap, dinobuton, binapacryl;

benzoylureas, e.g. fluazuron, penfluron,

amidine derivatives, e.g. chlormebuform, cymiazole, demiditraz

beehive varroa acaricides, for example organic acids, e.g. formic acid,oxalic acid.

Illustrative active compounds from the group of the endoparasiticides,as mixing components, include, but are not limited to, activeanthelmintic ingredients and active antiprotozoic ingredients.

The active anthelmintic ingredients include, but are not limited to, thefollowing active nematicidal, trematicidal and/or cestocidalingredients:

from the class of the macrocyclic lactones, for example: eprinomectin,abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin,latidectin, milbemectin, ivermectin, emamectin, milbemycin;

from the class of the benzimidazoles and probenzimidazoles, for example:oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole,oxfendazole, netobimin, fenbendazole, febantel, thiabendazole,cyclobendazole, cambendazole, albendazole sulfoxide, albendazole,flubendazole; from the class of the depsipeptides, preferably cyclicdepsipeptides, especially 24-membered cyclic depsipeptides, for example:emodepside, PF1022A;

from the class of the tetrahydropyrimidines, for example: morantel,pyrantel, oxantel;

from the class of the imidazothiazoles, for example: butamisole,levamisole, tetramisole;

from the class of the aminophenylamidines, for example: amidantel,deacylated amidantel (dAMD), tribendimidine;

from the class of the aminoacetonitriles, for example: monepantel;

from the class of the paraherquamides, for example: paraherquamide,derquantel;

from the class of the salicylanilides, for example: tribromsalan,bromoxanide, brotianide, clioxanide, closantel, niclosamide,oxyclozanide, rafoxanide;

from the class of the substituted phenols, for example: nitroxynil,bithionol, disophenol, hexachlorophene, niclofolan, meniclopholan;

from the class of the organophosphates, for example: trichlorfon,naphthalofos, dichlorvos/DDVP, crufomate, coumaphos, haloxon;

from the class of the piperazinones/quinolines, for example:praziquantel, epsiprantel; from the class of the piperazines, forexample: piperazine, hydroxyzine;

from the class of the tetracyclines, for example: tetracycline,chlorotetracycline, doxycycline, oxytetracycline, rolitetracycline;

from various other classes, for example: bunamidine, niridazole,resorantel, omphalotin, oltipraz, nitroscanate, nitroxynil, oxamniquin,mirasan, miracil, lucanthon, hycanthon, hetolin, emetin,diethylcarbamazine, dichlorophen, diamfenetide, clonazepam, bephenium,amoscanate, clorsulon.

Active antiprotozoic ingredients include, but are not limited to, thefollowing active compounds: from the class of the triazines, forexample: diclazuril, ponazuril, letrazuril, toltrazuril; from the classof polyether ionophores, for example: monensin, salinomycin,maduramicin, narasin; from the class of the macrocyclic lactones, forexample: milbemycin, erythromycin;

from the class of the quinolones, for example: enrofloxacin,pradofloxacin;

from the class of the quinines, for example: chloroquine;

from the class of the pyrimidines, for example: pyrimethamine;

from the class of the sulfonamides, for example: sulfaquinoxaline,trimethoprim, sulfaclozin;

from the class of the thiamines, for example: amprolium;

from the class of the lincosamides, for example: clindamycin;

from the class of the carbanilides, for example: imidocarb;

from the class of the nitrofurans, for example: nifurtimox;

from the class of the quinazolinone alkaloids, for example:halofuginone;

from various other classes, for example: oxamniquin, paromomycin;

from the class of the vaccines or antigens from microorganisms, forexample: Babesia canis rossi, Eimeria tenella, Eimeria praecox, Eimerianecatrix, Eimeria mitis, Eimeria maxima, Eimeria brunetti, Eimeriaacervulina, Babesia canis vogeli, Leishmania infantum, Babesia caniscanis, Dictyocaulus viviparus.

All the mixing components mentioned, as the case may be, may also formsalts with suitable bases or acids if they are capable of doing so onthe basis of their functional groups.

Vector Control

The compounds of the formula (I) can also be used in vector control. Inthe context of the present invention, a vector is an arthropod,especially an insect or arachnid, capable of transmitting pathogens, forexample viruses, worms, single-cell organisms and bacteria, from areservoir (plant, animal, human, etc.) to a host. The pathogens can betransmitted either mechanically (for example trachoma by non-stingingflies) onto a host or after injection into a host (for example malariaparasites by mosquitoes).

Examples of vectors and the diseases or pathogens they transmit are:

1) Mosquitoes

-   -   Anopheles: malaria, filariasis;    -   Culex: Japanese encephalitis, filariasis, other viral diseases,        transmission of other worms;    -   Aedes: yellow fever, dengue fever, further viral disorders,        filariasis;    -   Simuliidae: transmission of worms, especially Onchocerca        volvulus;    -   Psychodidae: transmission of leishmaniasis

2) Lice: skin infections, epidemic typhus;

3) Fleas: plague, endemic typhus, tapeworms;

4) Flies: sleeping sickness (trypanosomiasis); cholera, other bacterialdiseases;

5) Mites: acariosis, epidemic typhus, rickettsialpox, tularaemia, SaintLouis encephalitis, tick-borne encephalitis (TBE), Crimean-Congohaemorrhagic fever, borreliosis;

6) Ticks: borellioses such as Borrelia bungdorferi sensu lato., Borreliaduttoni, tick-borne encephalitis, Q fever (Coxiella burnetii),babesioses (Babesia canis canis), ehrlichiosis.

Examples of vectors in the context of the present invention are insects,for example aphids, flies, leafhoppers or Thrips, which can transmitplant viruses to plants. Other vectors capable of transmitting plantviruses are spider mites, lice, beetles and nematodes.

Further examples of vectors in the context of the present invention areinsects and arachnids such as mosquitoes, especially of the generaAedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A.dirus (malaria) and Culex, Psychodidae such as Phlebotomus, Lutzomyia,lice, fleas, flies, mites and ticks, which can transmit pathogens toanimals and/or humans.

Vector control is also possible if the compounds of the formula (I) areresistance-breaking.

Compounds of the formula (I) are suitable for use in the prevention ofdiseases and/or pathogens transmitted by vectors. Thus, a further aspectof the present invention is the use of compounds of the formula (I) forvector control, for example in agriculture, in horticulture, in forests,in gardens and in leisure facilities, and also in the protection ofmaterials and stored products.

Protection of Industrial Materials

The compounds of the formula (I) are suitable for protecting industrialmaterials against attack or destruction by insects, for example from theorders of Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera andZygentoma.

Industrial materials in the present context are understood to meaninanimate materials, such as preferably plastics, adhesives, sizes,papers and cards, leather, wood, processed wood products and coatingcompositions. The use of the invention for protection of wood isparticularly preferred.

In a further embodiment, the compounds of the formula (I) are usedtogether with at least one further insecticide and/or at least onefungicide.

In a further embodiment, the compounds of the formula (I) take the formof a ready-to-use pesticide, meaning that they can be applied to thematerial in question without further modifications. Useful furtherinsecticides or fungicides especially include those mentioned above.

Surprisingly, it has also been found that the compounds of the formula(I) can be employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signalling systems, against fouling. It isequally possible to use the compounds of the formula (I), alone or incombinations with other active compounds, as antifouling agents.

Control of Animal Pests in the Hygiene Sector

The compounds of the formula (I) are suitable for controlling animalpests in the hygiene sector. More particularly, the invention can beused in the domestic protection sector, in the hygiene protection sectorand in the protection of stored products, particularly for control ofinsects, arachnids, ticks and mites encountered in enclosed spaces, forexample dwellings, factory halls, offices, vehicle cabins, animalbreeding facilities. For controlling animal pests, the compounds of theformula (I) are used alone or in combination with other active compoundsand/or auxiliaries. They are preferably used in domestic insecticideproducts. The compounds of the formula (I) are effective againstsensitive and resistant species, and against all developmental stages.

These pests include, for example, pests from the class Arachnida, fromthe orders Scorpiones, Araneae and Opiliones, from the classes Chilopodaand diplopoda, from the class insecta the order Blattodea, from theorders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera,Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria orOrthoptera, Siphonaptera and Zygentoma and from the class Malacostracathe order Isopoda.

Application is effected, for example, in aerosols, unpressurized sprayproducts, for example pump and atomizer sprays, automatic foggingsystems, foggers, foams, gels, evaporator products with evaporatortablets made of cellulose or plastic, liquid evaporators, gel andmembrane evaporators, propeller-driven evaporators, energy-free, orpassive, evaporation systems, moth papers, moth bags and moth gels, asgranules or dusts, in baits for spreading or bait stations.

PREPARATION EXAMPLES1-[5-Ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-2-pyridyl]-3-methylurea(I-4)

Under argon, 346 mg (0.68 mmol) of2-(6-chloro-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridinewere dissolved in 20 ml of degassed dioxane, 62.5 mg (0.81 mmol) ofN-methylurea, 333 mg (1.02 mmol) of caesium carbonate, 39.4 mg (0.06mmol) of 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene (xanthphos) and31.2 mg (0.03 mmol) of tris(dibenzylideneacetone)dipalladium(0) wereadded and the mixture was stirred at 80° C. for 3 h. The reactionmixture was then filtered through a silica gel cartridge rinsing withethyl acetate. The mother liquor was washed with sodium chloridesolution and dried over sodium sulfate, and the solvent was thendistilled off under reduced pressure. The residue was purified by columnchromatography purification on silica gel with a cyclohexane ethylacetate mixture (6:4) as mobile phase.

(log P (neutral): 1.83; MH⁺: 443; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.16(t, 3H), 2.70 (d, 3H), 3.61 (q, 2H), 3.87 (s, 3H), 6.94 (m, 1H), 8.12(d, 1H), 8.28 (s, 1H), 8.34 (d, 1H), 9.27 (s, 1H), 10.06 (s, 1H).

2-(6-Chloro-3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine

900 mg (2.41 mmol) of2-(6-chloro-3-ethylsulfanyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridinewere dissolved in 50 ml of dichloromethane, 555.6 mg (12.0 mmol) offormic acid and 1.64 g (16.8 mmol) of 35% strength hydrogen peroxidewere added at room temperature and the mixture was then stirred at roomtemperature for 5 h. The mixture was diluted with water and sodiumbisulfite solution was added, the mixture was stirred for 1 h andsaturated sodium hydrogencarbonate solution was then added. The organicphase was separated off, the aqueous phase was extracted twice withdichloromethane and the combined organic phases were then freed of thesolvent under reduced pressure. The residue was purified by columnchromatography purification by means of preparative HPLC with awater/acetonitrile gradient as mobile phase.

(log P (neutral): 2.54; MH⁺: 405; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 1.20(t, 3H), 3.77 (q, 2H), 3.91 (s, 3H), 8.13 (d, 1H), 8.32 (s, 1H), 8.56(d, 1H), 9.30 (s, 1H).

2-(6-Chloro-3-ethylsulfanyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine

4.00 g (10.7 mmol) of2-(3,6-dichloro-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridinewere dissolved in 60 ml of tetrahydrofuran, 446 mg (11.1 mmol) of sodiumhydride were added at −5° C. and the mixture was stirred at 0° C. for 30minutes. 733 mg (11.8 mmol) ethanethiol were then added dropwise over 30minutes at −5° C., the cooling bath was removed and the mixture wasstirred at room temperature for 2 h. The reaction mixture was hydrolysedwith water, the organic phase was separated off and the aqueous phasewas extracted twice with ethyl acetate. The organic phases werecombined, washed with sodium chloride solution and dried over sodiumsulfate, and the solvent was then distilled off under reduced pressure.The residue is purified by trituration with methyl tert-butylketone/dichloromethane 25:1.

(log P (neutral): 3.06; MH⁺: 373; ¹H-NMR (400 MHz, CD3CN) δ ppm: 1.25(t, 3H), 2.98 (q, 2H), 3.98 (s, 3H), 7.56 (d, 1H), 7.95 (d, 1H), 8.15(s, 1H), 9.06 (s, 1H).

2-(3,6-Dichloro-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine

20 g (104.6 mmol) of N³-methyl-6-(trifluoromethyl)pyridine-3,4-diamine,25.11 g (130.8 mmol) of 3,6-dichloropyridine-2-carboxylic acid and 20.06g (104.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimidehydrochloride (EDCI) were stirred in 200 ml of pyridine at 120° C. for 8h. The reaction mixture was freed of solvent under reduced pressure,water was added and the mixture was extracted three times with ethylacetate. The organic phases were combined and dried over sodium sulfate,and the solvent was then distilled off under reduced pressure. Theresidue was purified by column chromatography using, as mobile phase, acyclohexane/ethyl acetate gradient.

(log P (neutral): 2.81; MH⁺: 347; ¹H-NMR (400 MHz, D₆-DMSO) δ ppm: 3.99(s, 3H), 7.89 (d, 1H), 8.32 (s, 1H), 8.35 (d, 1H), 9.28 (s, 1H).

In analogy to the examples and according to the above-describedpreparation processes, the following compounds of the formula (I) can beobtained:

Ex- am- ple Structure I-1

I-2

I-3

I-4

I-5

I-6

I-7

I-8

I-9

I-10

I-11

I-12

I-13

I-14

I-15

The log P values are measured according to EEC Directive 79/831 AnnexV.A8 by HPLC (high-performance liquid chromatography) on areversed-phase column (C 18). Temperature: 55° C.

The LC-MS determination in the acidic range is effected at pH 2.7 with0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid)as mobile phases; linear gradient from 10% acetonitrile to 95%acetonitrile. Called log P (HCOOH) in the table.

The LC-MS determination in the neutral range is effected at pH 7.8 with0.001 molar aqueous ammonium bicarbonate solution and acetonitrile asmobile phases; linear gradient from 10% acetonitrile to 95%acetonitrile. Called log P (neutral) in the table.

Calibration is carried out using unbranched alkan-2-ones (having 3 to 16carbon atoms) with known log P values (log P values determined on thebasis of the retention times by linear interpolation between twosuccessive alkanones).

The NMR data of selected examples are listed either in conventional form(6 values, multiplet splitting, number of hydrogen atoms) or as NMR peaklists.

In each case, the solvent in which the NMR spectrum was recorded isstated.

NMR Peak List Method

The ¹H NMR data of selected examples are stated in the form of ¹H NMRpeak lists. For each signal peak, first the δ value in ppm and then thesignal intensity in round brackets are listed. The pairs of 6value-signal intensity numbers for different signal peaks are listedwith separation from one another by semicolons.

The peak list for one example therefore takes the form of:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

The intensity of sharp signals correlates with the height of the signalsin a printed example of an NMR spectrum in cm and shows the true ratiosof the signal intensities. In the case of broad signals, several peaksor the middle of the signal and the relative intensity thereof may beshown in comparison to the most intense signal in the spectrum.

For calibration of the chemical shift of ¹H NMR spectra, we usetetramethylsilane and/or the chemical shift of the solvent, particularlyin the case of spectra which are measured in DMSO. Therefore, thetetramethylsilane peak may but need not occur in NMR peak lists.

The lists of the ¹H NMR peaks are similar to the conventional ¹H NMRprintouts and thus usually contain all peaks listed in a conventionalNMR interpretation.

In addition, like conventional ¹H NMR printouts, they may show solventsignals, signals of stereoisomers of the target compounds which arelikewise provided by the invention, and/or peaks of impurities.

In the reporting of compound signals within the delta range of solventsand/or water, our lists of ¹H NMR peaks show the standard solvent peaks,for example peaks of DMSO in DMSO-D₆ and the peak of water, whichusually have a high intensity on average.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities usually have a lower intensity on average than the peaks ofthe target compounds (for example with a purity of >90%).

Such stereoisomers and/or impurities may be typical of the particularpreparation process. Their peaks can thus help in identifyingreproduction of our preparation process with reference to “by-productfingerprints”.

An expert calculating the peaks of the target compounds by known methods(MestreC, ACD simulation, but also with empirically evaluated expectedvalues) can, if required, isolate the peaks of the target compounds,optionally using additional intensity filters. This isolation would besimilar to the peak picking in question in conventional ¹H NMRinterpretation.

Further details of ¹H NMR peak lists can be found in the ResearchDisclosure Database Number 564025.

Example I-1: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.951 (2.74); 9.309(0.35); 9.278 (4.06); 8.382 (0.32); 8.346 (2.73); 8.324 (3.63); 8.313(0.77); 8.286 (4.41); 8.171 (3.14); 8.148 (2.52); 7.007 (0.68); 6.993(1.24); 6.98 (0.63); 4.038 (0.58); 4.02 (0.59); 3.952 (1.14); 3.869(16); 3.825 (0.81); 3.643 (0.96); 3.625 (3.24); 3.607 (3.26); 3.588(0.97); 3.318 (197.34); 3.201 (0.5); 3.183 (1.68); 3.169 (1.95); 3.151(1.74); 3.134 (0.52); 2.675 (0.69); 2.67 (0.93); 2.524 (2.11); 2.51(54.48); 2.506 (115.09); 2.501 (160.6); 2.497 (118.72); 2.493 (56.23);2.333 (0.66); 2.328 (0.97); 2.324 (0.7); 1.988 (2.5); 1.615 (0.32);1.398 (0.34); 1.193 (0.85); 1.183 (3.55); 1.175 (1.8); 1.164 (7.99);1.158 (1.24); 1.146 (3.41); 1.132 (0.46); 1.072 (4.2); 1.054 (8.99);1.036 (4.02); 0.146 (0.47); 0.008 (3.36); 0 (115.39); −0.008 (3.89);−0.15 (0.47) Example I-2: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 10.218(3.32); 9.276 (4.52); 8.378 (2.79); 8.355 (3.37); 8.29 (4.94); 8.127(2.77); 8.105 (2.42); 7.412 (0.71); 7.398 (1.36); 7.384 (0.73); 5.757(9.29); 3.875 (16); 3.659 (1.04); 3.64 (3.38); 3.622 (3.43); 3.604(1.06); 3.445 (1.01); 3.429 (2.79); 3.414 (2.87); 3.398 (1.1); 3.319(14.36); 2.73 (2.45); 2.714 (4.95); 2.698 (2.26); 2.671 (0.5); 2.506(63.07); 2.501 (83.1); 2.497 (63.36); 2.328 (0.47); 2.324 (0.39); 1.989(1.16); 1.185 (3.82); 1.166 (8.25); 1.157 (1.08); 1.148 (3.7); 0 (29.82)Example I-3: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 10.17 (3); 9.276 (4.28);8.365 (2.84); 8.342 (3.44); 8.315 (1.9); 8.286 (4.62); 8.106 (2.44);8.083 (2.17); 7.452 (0.59); 7.438 (1.05); 7.425 (0.66); 7.393 (0.35);7.382 (0.39); 3.952 (0.35); 3.902 (16); 3.87 (15.47); 3.824 (0.5); 3.652(0.98); 3.633 (3.32); 3.615 (3.5); 3.596 (1.49); 3.575 (1.11); 3.56(1.31); 3.547 (1.05); 3.529 (0.86); 3.514 (0.59); 3.32 (64.34); 3.296(0.85); 3.011 (0.47); 2.992 (0.68); 2.978 (1.07); 2.972 (0.76); 2.96(0.95); 2.944 (0.59); 2.843 (0.66); 2.829 (1.45); 2.814 (0.79); 2.796(1.02); 2.782 (0.44); 2.675 (0.66); 2.67 (0.92); 2.666 (0.66); 2.52(21.93); 2.51 (59.23); 2.506 (120); 2.502 (157.66); 2.497 (112.46);2.332 (0.64); 2.328 (0.9); 2.324 (0.65); 1.648 (0.39); 1.183 (3.6);1.165 (8.04); 1.146 (3.55); 1.132 (0.33); 0.008 (1.76); 0 (53.42);−0.008 (2.06) Example I-4: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 10.062(2.36); 9.274 (4.04); 8.346 (2.83); 8.323 (3.47); 8.313 (0.45); 8.283(4.2); 8.128 (2.62); 8.105 (2.19); 6.948 (0.95); 6.937 (0.91); 4.056(0.33); 4.038 (0.99); 4.02 (0.95); 4.003 (0.37); 3.865 (16); 3.64(0.96); 3.622 (3.15); 3.603 (3.23); 3.585 (0.93); 3.317 (138.48); 2.708(6.54); 2.697 (6.53); 2.675 (0.62); 2.671 (0.8); 2.666 (0.59); 2.524(1.77); 2.51 (44.79); 2.506 (95.76); 2.501 (134.8); 2.497 (100.65);2.492 (48.08); 2.332 (0.57); 2.328 (0.78); 2.323 (0.58); 1.988 (4.21);1.193 (1.24); 1.182 (3.39); 1.175 (2.63); 1.164 (7.83); 1.158 (1.75);1.145 (3.4); 0.146 (0.32); 0.008 (2.43); 0 (80.13); −0.008 (2.59); −0.15(0.37) Example I-5: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 10.07 (2.43); 9.297(3.64); 8.353 (2.49); 8.331 (2.95); 8.294 (3.9); 8.042 (1.81); 8.02(1.63); 7.452 (0.78); 3.877 (13.95); 3.66 (0.8); 3.641 (2.81); 3.623(2.87); 3.604 (0.85); 3.376 (0.89); 3.363 (2.69); 3.352 (2.63); 3.328(1.53); 3.32 (11.45); 3.303 (1.67); 3.291 (0.51); 3.109 (16); 2.524(0.58); 2.511 (15.95); 2.506 (33.96); 2.502 (46.08); 2.498 (33.79);2.493 (16.75); 1.989 (1.13); 1.187 (3.1); 1.174 (1.15); 1.168 (7); 1.157(0.72); 1.15 (3.04); 0.008 (0.59); 0 (19.2); −0.008 (0.75) Example I-6:¹H-NMR (400.0 MHz, d₆-DMSO): δ = 10.161 (2.7); 9.283 (3.85); 8.352(2.34); 8.329 (2.78); 8.315 (0.49); 8.286 (4.04); 8.029 (1.89); 8.006(1.68); 7.535 (0.9); 4.056 (0.35); 4.038 (1.02); 4.02 (1.05); 4.002(0.35); 3.953 (0.32); 3.869 (13.27); 3.824 (0.37); 3.644 (0.9); 3.626(2.86); 3.607 (2.9); 3.589 (0.91); 3.374 (0.89); 3.358 (2.43); 3.343(2.6); 3.319 (28.29); 2.67 (0.81); 2.573 (2.01); 2.557 (4.12); 2.54(2.03); 2.506 (114.87); 2.502 (142.97); 2.497 (108.98); 2.328 (0.81);2.048 (0.34); 1.989 (4.25); 1.944 (16); 1.192 (1.4); 1.183 (3.3); 1.175(3.03); 1.165 (7.04); 1.157 (2.19); 1.147 (3.17); 0.146 (0.42); 0(88.1); −0.15 (0.44) Example I-7: ¹H-NMR (400.0 MHz, d₆-DMSO): δ = 9.781(2.98); 9.281 (4.09); 8.349 (2.63); 8.326 (3.66); 8.313 (0.4); 8.286(4.33); 8.21 (3.47); 8.187 (2.68); 6.878 (1.27); 6.859 (1.24); 4.038(0.64); 4.02 (0.64); 3.87 (16); 3.831 (0.62); 3.814 (0.97); 3.797(0.98); 3.78 (0.64); 3.643 (0.94); 3.625 (3.22); 3.606 (3.27); 3.588(0.97); 3.319 (110.87); 3.295 (0.55); 2.675 (0.75); 2.67 (1.04); 2.666(0.77); 2.524 (2.7); 2.519 (4.09); 2.51 (58.43); 2.506 (123.3); 2.501(172.76); 2.497 (129.74); 2.492 (62.59); 2.333 (0.7); 2.328 (1); 2.323(0.73); 1.988 (2.71); 1.615 (0.62); 1.398 (2.01); 1.193 (0.84); 1.182(3.48); 1.175 (1.89); 1.164 (7.91); 1.157 (1.37); 1.145 (3.38); 1.107(15.26); 1.091 (15.17); 1.009 (0.37); 0.993 (0.37); 0.146 (0.98); 0.008(7.5); 0 (227.94); −0.008 (8.27); −0.15 (1.01) Example I-8: ¹H-NMR(400.0 MHz, d₆-DMSO): δ = 10.27 (3.14); 9.272 (4.26); 8.369 (2.58);8.346 (3.09); 8.283 (4.54); 8.094 (2.3); 8.071 (2.05); 7.438 (1.08);7.425 (0.69); 7.389 (0.34); 7.379 (0.41); 3.953 (0.32); 3.902 (16);3.864 (14.37); 3.824 (0.43); 3.653 (0.97); 3.635 (3.3); 3.616 (4.43);3.597 (3.38); 3.581 (1.05); 3.334 (2.52); 3.321 (43.53); 3.303 (1.86);2.972 (14.59); 2.671 (0.73); 2.506 (102.43); 2.502 (128.07); 2.498(93.41); 2.328 (0.72); 1.65 (0.39); 1.235 (0.42); 1.183 (3.47); 1.165(7.52); 1.146 (3.41); 0.008 (1.64); 0 (41.09) Example I-9: 1H-NMR (400.0MHz, d6-DMSO): δ = 9.2744 (2.2); 8.2775 (2.3); 8.2256 (1.7); 8.2028(1.8); 7.2238 (1.7); 7.2010 (1.7); 4.0379 (0.4); 4.0201 (0.4); 3.9072(8.2); 3.7020 (0.5); 3.6833 (1.7); 3.6649 (1.7); 3.6463 (0.5); 3.3207(21.6); 3.2071 (8.2); 2.9724 (0.4); 2.9399 (16.0); 2.8148 (0.6); 2.6706(0.4); 2.5237 (1.0); 2.5059 (54.5); 2.5015 (72.8); 2.4971 (52.7); 2.3282(0.4); 1.9887 (1.6); 1.2655 (1.0); 1.2008 (1.8); 1.1924 (0.7); 1.1824(4.1); 1.1748 (1.2); 1.1639 (1.8); 1.1572 (0.7); −0.0002 (9.1) ExampleI-10: 1H-NMR (400.0 MHz, d6-DMSO): δ = 9.2718 (4.6); 9.1363 (3.3);8.2820 (4.8); 8.2402 (4.6); 8.1402 (0.6); 3.8803 (16.0); 3.7082 (1.0);3.6898 (3.4); 3.6713 (3.5); 3.6527 (1.1); 3.4140 (2.4); 3.3203 (16.7);2.6702 (0.6); 2.5055 (76.8); 2.5012 (102.9); 2.4970 (77.1); 2.3631(12.3); 2.3278 (0.6); 2.3238 (0.5); 2.0741 (0.6); 1.8451 (4.1); 1.2091(3.7); 1.1908 (8.1); 1.1722 (3.6); 0.1457 (0.3); 0.0077 (2.6); −0.0002(71.0); −0.0083 (3.3) Example I-11: 1H-NMR (400.0 MHz, d6-DMSO): δ =9.2692 (4.5); 9.2260 (0.5); 9.0211 (2.8); 8.3155 (1.2); 8.2974 (1.1);8.2817 (4.9); 8.2377 (0.6); 8.1728 (4.1); 7.8092 (0.5); 6.5312 (0.3);3.9596 (0.4); 3.8824 (16.0); 3.8096 (1.7); 3.7116 (1.0); 3.6927 (3.3);3.6743 (3.4); 3.6559 (1.0); 3.4745 (0.4); 3.4551 (0.4); 3.3199 (226.1);2.7078 (7.4); 2.6962 (7.5); 2.6746 (2.6); 2.6703 (3.5); 2.6658 (2.6);2.6229 (0.4); 2.5235 (8.2); 2.5057 (456.6); 2.5013 (613.2); 2.4969(446.8); 2.4354 (11.6); 2.3517 (0.4); 2.3327 (2.5); 2.3279 (3.4); 2.3241(2.6); 2.2138 (1.3); 2.0746 (0.4); 2.0103 (0.5); 1.9893 (0.5); 1.4550(0.3); 1.2912 (0.4); 1.2361 (2.7); 1.2120 (0.7); 1.2003 (3.8); 1.1819(8.1); 1.1633 (3.7); 1.1499 (0.7); 1.1315 (1.0); 1.1138 (0.5); 0.8549(0.7); 0.1462 (1.4); 0.0077 (9.5); −0.0002 (279.2); −0.0081 (12.1);−0.1498 (1.4) Example I-12: 1H-NMR (400.0 MHz, d6-DMSO): δ = 9.2794(4.2); 8.3128 (3.2); 8.2894 (5.7); 8.0338 (3.4); 8.0109 (3.0); 7.8984(1.2); 7.8873 (1.2); 4.0383 (0.6); 4.0205 (0.6); 3.9036 (16.0); 3.7199(1.0); 3.7015 (3.3); 3.6830 (3.4); 3.6647 (1.0); 3.4078 (0.3); 3.3843(16.1); 3.3207 (40.9); 2.7399 (7.7); 2.7289 (7.7); 2.6757 (0.4); 2.6712(0.5); 2.6668 (0.4); 2.5065 (65.1); 2.5020 (84.2); 2.4976 (62.2); 2.3329(0.4); 2.3287 (0.5); 2.3244 (0.4); 1.9888 (2.4); 1.2069 (3.6); 1.1885(8.2); 1.1750 (2.0); 1.1700 (3.6); 1.1574 (0.7); 0.0078 (2.5); −0.0002(58.4); −0.0079 (2.9) Example I-13: 1H-NMR (400.0 MHz, d6-DMSO): δ =9.3515 (4.3); 9.0153 (7.4); 9.0064 (0.4); 8.7868 (3.3); 8.7649 (4.0);8.5030 (3.9); 8.4810 (3.5); 8.3362 (4.6); 8.0675 (1.8); 7.6937 (1.6);7.3327 (0.5); 7.3245 (0.4); 5.7560 (1.2); 4.1954 (0.4); 4.0100 (16.0);3.8854 (1.0); 3.8670 (3.5); 3.8485 (3.4); 3.8301 (1.1); 3.5678 (0.4);3.3307 (38.4); 2.6755 (0.5); 2.6709 (0.7); 2.6667 (0.5); 2.5105 (46.7);2.5063 (90.7); 2.5018 (118.5); 2.4974 (87.6); 2.3329 (0.5); 2.3286(0.7); 2.3242 (0.5); 1.5995 (0.6); 1.2620 (3.8); 1.2436 (8.5); 1.2251(3.7); 0.0077 (1.9); −0.0004 (43.0); −0.0084 (1.8) Example I-14: 1H-NMR(400.0 MHz, d6-DMSO): δ = 9.7380 (3.4); 9.2820 (4.3); 8.3583 (1.7);8.3356 (4.4); 8.3095 (4.9); 8.2867 (6.6); 4.0556 (0.9); 4.0379 (2.9);4.0201 (2.9); 4.0023 (1.0); 3.8636 (16.0); 3.8244 (0.6); 3.6039 (1.0);3.5856 (3.4); 3.5671 (3.4); 3.5487 (1.1); 3.4393 (2.4); 3.3207 (57.7);2.6706 (0.5); 2.6659 (0.4); 2.5058 (59.5); 2.5014 (79.9); 2.4969 (62.3);2.3326 (0.4); 2.3281 (0.5); 1.9886 (12.2); 1.8419 (3.6); 1.1924 (3.4);1.1747 (9.4); 1.1572 (10.7); 1.1391 (3.6); 0.0078 (1.4); −0.0002 (35.4);−0.0081 (1.9) Example I-15: 1H-NMR (400.0 MHz, d6-DMSO): δ = 9.9032(2.3); 9.2827 (3.0); 8.3498 (1.8); 8.3272 (2.5); 8.2893 (3.2); 8.1958(2.8); 8.1731 (2.3); 3.8670 (11.7); 3.8241 (0.8); 3.6077 (0.7); 3.5893(2.4); 3.5708 (2.4); 3.5523 (0.7); 3.3194 (46.3); 2.9725 (16.0); 2.9558(0.6); 2.6750 (0.4); 2.6704 (0.6); 2.6659 (0.4); 2.5235 (1.9); 2.5100(36.8); 2.5058 (73.8); 2.5013 (97.1); 2.4969 (71.3); 2.3324 (0.4);2.3281 (0.6); 2.3236 (0.4); 1.9886 (0.4); 1.1766 (2.7); 1.1582 (5.9);1.1398 (2.5); 1.1315 (0.6); 0.0080 (1.8); −0.0002 (49.0); −0.0084 (2.1)

USE EXAMPLES

Ctenocephalides felis—In Vitro Contact Tests with Adult Cat Fleas

For the coating of the test tubes, 9 mg of active compound are firstdissolved in 1 ml of acetone p.a. and then diluted to the desiredconcentration with acetone p.a. 250 μl of the solution are distributedhomogeneously on the inner walls and the base of a 25 ml glass tube byturning and rocking on an orbital shaker (rocking rotation at 30 rpm for2 h). With 900 ppm of active compound solution and internal surface area44.7 cm², given homogeneous distribution, an area-based dose of 5 μg/cm²is achieved.

After the solvent has evaporated off, the tubes are populated with 5-10adult cat fleas (Ctenocephalides felis), sealed with a perforatedplastic lid and incubated in a horizontal position at room temperatureand ambient humidity. After 48 h, efficacy is determined. To this end,the tubes are stood upright and the fleas are knocked to the base of thetube. Fleas which remain motionless at the base or move in anuncoordinated manner are considered to be dead or moribund.

A substance shows good efficacy against Ctenocephalides felis if atleast 80% efficacy was achieved in this test at an application rate of 5μg/cm². 100% efficacy means that all the fleas were dead or moribund. 0%efficacy means that no fleas were harmed.

In this test, for example, the following compound from the preparationexamples shows an efficacy of 100% at an application rate of 5 μg/cm²(=500 g/ha): I-4

Ctenocephalides felis—Oral Test

Solvent: dimethyl sulfoxide

To produce a suitable active compound preparation, 10 mg of activecompound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution withcitrated cattle blood gives the desired concentration.

About 20 unfed adult cat fleas (Ctenocephalides felis) are placed into achamber which is closed at the top and bottom with gauze. A metalcylinder whose bottom end is closed with parafilm is placed onto thechamber. The cylinder contains the blood/active compound preparation,which can be imbibed by the fleas through the parafilm membrane.

After 2 days, the kill in % is determined. 100% means that all of thefleas have been killed; 0% means that none of the fleas have beenkilled.

In this test, for example, the following compound from the preparationexamples shows an efficacy of 100% at an application rate of 100 ppm:I-1, I-2, I-3, I-4, I-7, I-8 In this test, for example, the followingcompound from the preparation examples shows an efficacy of 80% at anapplication rate of 100 ppm: I-5

Lucilia cuprina Test

Solvent: dimethyl sulfoxide

To produce a suitable active compound preparation, 10 mg of activecompound are mixed with 0.5 ml of dimethyl sulfoxide, and theconcentrate is diluted with water to the desired concentration.

About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) aretransferred into a test vessel containing minced horsemeat and theactive compound preparation of the desired concentration.

After 2 days, the kill in % is determined. 100% means that all thelarvae have been killed; 0% means that no larvae have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 100 ppm:I-4, I-5

Meloidogyne incognita Test

Solvent: 125.0 parts by weight of acetone

To produce a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amount of solvent and theconcentrate is diluted to the desired concentration with water. Vesselsare filled with sand, active compound solution, an egg/larvae suspensionof the southern root-knot nematode (Meloidogyne incognita) and lettuceseeds. The lettuce seeds germinate and the plants develop. The gallsdevelop on the roots.

After 14 days, the nematicidal efficacy in % is determined by theformation of galls. 100% means that no galls were found; 0% means thatthe number of galls on the treated plants corresponds to the untreatedcontrol.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 ppm: I-1,I-2, I-5, I-15

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 20 ppm: I-3,I-7

Myzus persicae—Spray Test

Solvent: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound preparation of the desired concentration.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compound from the preparationexamples shows an efficacy of 100% at an application rate of 500 g/ha:I-5

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 500 g/ha:I-1, I-2, I-4

In this test, for example, the following compound from the preparationexamples shows an efficacy of 100% at an application rate of 100 g/ha:I-3

In this test, for example, the following compounds from the preparationexamples show an efficacy of 90% at an application rate of 100 g/ha:1-6, I-8, I-12, I-13, I-14, I-15

Myzus persicae—Oral Test

Solvent: 100 parts by weight of acetone

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved with the stated parts by weight of solventand made up to the desired concentration with water.

50 μl of the active compound preparation are transferred into microtitreplates and made up to a final volume of 200 μl with 150 μl of IPL41insect medium (33%+15% sugar). Subsequently, the plates are sealed withparafilm, which a mixed population of green peach aphids (Myzuspersicae) within a second microtitre plate is able to puncture andimbibe the solution.

After 5 days, the efficacy in % is determined. 100% means that all theaphids have been killed; 0% means that no aphids have been killed.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 20 ppm: I-2,I-3, I-5, I-6, I-8

In this test, for example, the following compound from the preparationexamples show an efficacy of 100% at an application rate of 4 ppm: I-2,I-3, I-5, I-6, I-14, I-15

In this test, for example, the following compound from the preparationexamples show an efficacy of 90% at an application rate of 4 ppm: I-8,I-13

Phaedon cochleariae—Spray Test

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active compound preparation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the efficacy in % is determined. 100% means that all thebeetle larvae have been killed; 0% means that no beetle larvae have beenkilled.

In this test, for example, the following compounds from the preparationexamples show an efficacy of 100% at an application rate of 500 g/ha:I-1, I-4 In this test, for example, the following compounds from thepreparation examples show an efficacy of 100% at an application rate of100 g/ha: 1-6, I-15

Tetranychus urticae—Spray Test, OP-Resistant

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of bean leaves (Phaseolus vulgaris) infested with all stages ofthe greenhouse red spider mite (Tetranychus urticae) are sprayed with anactive compound preparation of the desired concentration.

After 6 days, the efficacy in % is determined. 100% means that all thespider mites have been killed; 0% means that no spider mites have beenkilled.

In this test, for example, the following compounds from the preparationexamples shows an efficacy of 100% at an application rate of 100 g/ha:1-3, I-8 In this test, for example, the following compound from thepreparation examples shows an efficacy of 90% at an application rate of100 g/ha: I-1 In this test, for example, the following compound from thepreparation examples shows an efficacy of 70% at an application rate of100 g/ha: I-6

COMPARATIVE EXAMPLES

Phaedon cochleariae—Spray Test (PHAECO)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active compound preparation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After the desired period of time, the efficacy in % is determined. 100%means that all the beetle larvae have been killed; 0% means that nobeetle larvae have been killed.

In this test, for example, the following compounds from the preparationexamples show superior efficacy to the prior art: see table.

Myzus persicae—Spray Test (MYZUPE)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of Chinese cabbage leaves (Brassica pekinensis) infested by allstages of the green peach aphid (Myzus persicae) are sprayed with anactive compound preparation of the desired concentration.

After the desired period of time, the efficacy in % is determined. 100%means that all the aphids have been killed; 0% means that no aphids havebeen killed.

In this test, for example, the following compounds from the preparationexamples show superior efficacy to the prior art: see table.

Tetranychus urticae—Spray Test; OP-Resistant (TETRUR)

Solvent: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater.

Discs of bean leaves (Phaseolus vulgaris) infested with all stages ofthe greenhouse red spider mite (Tetranychus urticae) are sprayed with anactive compound preparation of the desired concentration.

After the desired period of time, the efficacy in % is determined. 100%means that all the spider mites have been killed; 0% means that nospider mites have been killed.

In this test, for example, the following compounds from the preparationexamples show superior efficacy to the prior art: see table.

Nezara viridula—Spray Test (NEZAVI)

Solvent: 52.5 parts by weight of acetone

-   -   7 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater. If the addition of ammonium salts or/and penetrants is required,these are each added in a concentration of 1000 ppm to the formulationsolution.

Barley plants (Hordeum vulgare) infected with larvae of the Southerngreen shield bug (Nezara viridula) are sprayed with an active compoundpreparation of the desired concentration.

After the desired period of time, the efficacy in % is determined. 100%means that all of the shield bugs have been killed; 0% means that noneof the shield bugs have been killed.

In this test, for example, the following compounds from the preparationexamples show superior efficacy to the prior art: see table.

Nilaparvata lugens—Spray Test (NILALU)

Solvent: 52.5 parts by weight of acetone

-   -   7 parts by weight of dimethylformamide

Emulsifier: alkylaryl polyglycol ether

To produce a suitable active compound preparation, 1 part by weight ofactive compound is dissolved with the specified parts by weight ofsolvent and made up to the desired concentration with water containingan emulsifier concentration of 1000 ppm. To produce further testconcentrations, the formulation is diluted with emulsifier-containingwater. If the addition of ammonium salts or/and penetrants is required,these are each added in a concentration of 1000 ppm to the formulationsolution.

Rice plants (Oryza sativa) are sprayed with an active compoundpreparation of the desired concentration and then populated with larvaeof the brown planthopper (Nilaparvata lugens).

After the desired period of time, the efficacy in % is determined. 100%means that all of the planthoppers have been killed; 0% means that noneof the planthoppers have been killed.

In this test, for example, the following compounds from the preparationexamples show superior efficacy to the prior art: see table.

TABLE Substance Structure Object concentration % efficacy dat ExampleNo. I-4 according to the invention

NEZAVI  20 g/ha 100 4 dat Example No. I-49 known from WO 2015/121136

NEZAVI  20 g/ha  0 4 dat Example No. I-1 according to the invention

PHAECO TETRUR  20 g/ha 500 g/ha 100 g/ha  83  90  90 7 dat 6 dat 6 datExample No. 13 known from WO 2016/124557

PHAECO TETRUR  20 g/ha 500 g/ha 100 g/ha  50  70  0 7 dat 6 dat 6 datExample No. I-12 according to the invention

NILALU MYZUPE  4 g/ha  20 g/ha  90  90 4 dat 5 dat Example No. 69 knownfrom WO 2016/124557

NILALU MYZUPE  4 g/ha  20 g/ha  0  0 4 dat 5 dat dat = days aftertreatment

The invention claimed is:
 1. A compound of formula (I)

wherein A¹ represents nitrogen, ═N⁺(O⁻)— or ═C(R⁴)—, A² represents—N(R⁵)—, oxygen or sulfur, A³ represents oxygen or sulfur, R¹ represents(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,(C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl,(C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,(C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl,halo-(C₃-C₈)-cycloalkyl, amino, (C₁-C₆)-alkylamino,di-(C₁-C₆)-alkylamino, (C₃-C₈)-cycloalkylamino,(C₁-C₆)-alkylcarbonylamino, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)alkyl,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonylamino,aminosulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl,di-(C₁-C₆)-alkylaminosulfonyl-(C₁-C₆)-alkyl, or represents(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₈)-cycloalkyl, each of which is optionally mono- or polysubstitutedby identical or different substituents from the group consisting ofaryl, hetaryl and heterocyclyl, where aryl, hetaryl or heterocyclyl mayeach optionally be mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen, cyano, nitro,hydroxy, amino, carboxy, carbamoyl, aminosulfonyl, (C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl,(C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylsulfimino,(C₁-C₆)-alkylsulfimino-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfimino-(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-alkylsulfoximino,(C₁-C₆)-alkylsulfoximino-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfoximino-(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-alkylcarbonyl, (C₃-C₆)-trialkylsilyl and benzyl, or R¹represents aryl or hetaryl, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, cyano, nitro, hydroxy, amino, carboxyl,carbamoyl, (C₁-C₆)-alkyl, (C₃-C₈)-cycloalkyl, (C₁-C₆)-alkoxy,(C₁-C₆)-haloalkyl, (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio,(C₁-C₆)-alkylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylsulfimino,(C₁-C₆)-alkylsulfimino-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfimino-(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-alkylsulfoximino,(C₁-C₆)-alkylsulfoximino-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfoximino-(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-alkylcarbonyl, and (C₃-C₆)-trialkylsilyl, or R¹ representsheterocyclyl, which is optionally mono- or polysubstituted by identicalor different substituents from the group consisting of halogen, cyano,nitro, hydroxy, amino, carboxyl, carbamoyl, (C₁-C₆)-alkyl,(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkoxy, (C₁-C₆)-alkylthio, (C₁-C₆)-alkylsulfinyl,(C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylsulfimino,(C₁-C₆)-alkylsulfimino-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfimino-(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-alkylsulfoximino,(C₁-C₆)-alkylsulfoximino-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfoximino-(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-alkylcarbonyl, (C₃-C₆)-trialkylsilyl, (═O) and (═O)₂, R², R³, R⁴and R⁶ independently of one another represent hydrogen, cyano, halogen,nitro, acetyl, hydroxy, amino, SCN, tri-(C₁-C₆)-alkylsilyl,(C₃-C₈)-cycloalkyl, (C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl,(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, halo-(C₃-C₈)-cycloalkyl,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,(C₁-C₆)-hydroxyalkyl, hydroxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl,(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl,(C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-cyanoalkoxy,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,(C₁-C₆)-alkylhydroxyimino, (C₁-C₆)-alkoxyimino,(C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,(C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,(C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl,(C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,(C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkylthiocarbonyl,(C₁-C₆)-haloalkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,(C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl,(C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,di-(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,(C₂-C₆)-alkenylaminocarbonyl, di-(C₂-C₆)-alkenylaminocarbonyl,(C₃-C₈)-cycloalkylaminocarbonyl, (C₁-C₆)-alkylsulfonylamino,(C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino, aminosulfonyl,(C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,(C₁-C₆)-alkylsulfoximino, aminothiocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkyl-aminothiocarbonyl,(C₃-C₈)-cycloalkylamino, NHCO—(C₁-C₆)-alkyl((C₁-C₆)-alkylcarbonylamino), SF₅ or represent aryl or hetaryl, each ofwhich is optionally mono- or polysubstituted by identical or differentsubstituents, where in the case of hetaryl at least one carbonyl groupmay optionally be present and/or where optional substituents are in eachcase as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxy,amino, SCN, tri-(C₁-C₆)-alkylsilyl, (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₁-C₆)-cyanoalkyl, (C₁-C₆)-hydroxyalkyl,hydroxycarbonyl-(C₁-C₆)-alkoxy, (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,(C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,(C₂-C₆)-cyanoalkynyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,(C₁-C₆)-cyanoalkoxy, (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alkylhydroxyimino,(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkyl-(C₁-C₆)-alkoxyimino,(C₁-C₆)-haloalkyl-(C₁-C₆)-alkoxyimino, (C₁-C₆)-alkylthio,(C₁-C₆)-haloalkylthio, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio,(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl,(C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyl,(C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfonyloxy,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-alkoxycarbonyl,(C₁-C₆)-haloalkoxycarbonyl, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₆)-alkyl-aminocarbonyl, (C₂-C₆)-alkenylaminocarbonyl,di-(C₂-C₆)-alkenylaminocarbonyl, (C₃-C₈)-cycloalkylaminocarbonyl,(C₁-C₆)-alkylsulfonylamino, (C₁-C₆)-alkylamino, di-(C₁-C₆)-alkylamino,aminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,di-(C₁-C₆)-alkylaminosulfonyl, (C₁-C₆)-alkylsulfoximino,aminothiocarbonyl, (C₁-C₆)-alkylaminothiocarbonyl,di-(C₁-C₆)-alkylaminothiocarbonyl, (C₃-C₈)-cycloalkylamino, R⁵represents (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-cyanoalkyl,(C₁-C₆)-hydroxyalkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkenyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkenyloxy-(C₁-C₆)-alkyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-cyanoalkenyl, (C₂-C₆)-alkynyl,(C₂-C₆)-alkynyloxy-(C₁-C₆)-alkyl, (C₂-C₆)-haloalkynyloxy-(C₁-C₆)-alkyl,(C₂-C₆)-haloalkynyl, (C₂-C₆)-cyanoalkynyl, (C₃-C₈)-cycloalkyl,(C₃-C₈)-cycloalkyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl,halo-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylcarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylcarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-alkyl, aminocarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylamino-(C₁-C₆)-alkyl, di-(C₁-C₆)-alkylamino-(C₁-C₆)-alkyl or(C₃-C₈)-cycloalkylamino-(C₁-C₆)-alkyl, R⁷ represents hydrogen orrepresents (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₁₂)-cycloalkyl-(C₁-C₆)-alkylor (C₄-C₁₂)-bicycloalkyl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where thesubstituents independently of one another may be selected from the groupconsisting of halogen, cyano, nitro, hydroxy, (C₁-C₆)-alkyl,(C₁-C₄)-haloalkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,(C₁-C₄)-alkylsulfonyl, (C₂-C₆)-alkoxycarbonyl, (C₂-C₆)-alkylcarbonyl,amino, (C₁-C₄)-alkylamino, di-(C₁-C₄-alkyl)amino,(C₃-C₆)-cycloalkylamino, a phenyl ring or a 3- or 6-membered aromatic,partially saturated or saturated heterocycle, where the phenyl ring orheterocycle may in each case optionally be mono- or polysubstituted byidentical or different substituents, and where the substituentsindependently of one another may be selected from the group consistingof (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-halocycloalkyl, halogen, cyano, NO₂, OH, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,(C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl,(C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylamino, di-(C₁-C₄-alkyl)amino,(C₃-C₆)-cycloalkylamino, (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,aminocarbonyl, (C₁-C₆-alkyl)aminocarbonyl,di-(C₁-C₄-alkyl)aminocarbonyl, R⁸ represents amino or(C₁-C₆)-alkylamino, di-(C₁-C₄)-alkylamino, (C₂-C₆)-alkenylamino,(C₂-C₆)-alkynylamino, (C₃-C₁₂)-cycloalkylamino,(C₃-C₁₂)-cycloalkyl-(C₁-C₆)-alkylamino, (C₄-C₁₂)-bicycloalkylamino orhydrazino, each of which is optionally mono- or polysubstituted byidentical or different substituents, where the substituentsindependently of one another may be selected from the group consistingof halogen, cyano, amino, nitro, hydroxy, (C═O)OH, (C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylsulfinyl,(C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylsulfimino,(C₁-C₄)-alkylsulfoximino, (C₂-C₆)-alkoxycarbonyl, (C₂-C₆)-alkylcarbonyl,(C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₆)-haloalkylthiocarbonyl, (C₁-C₆)-alkylcarbonylamino,aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₆)-alkylaminocarbonyl, aminothiocarbonyl,(C₁-C₆)-alkylaminothiocarbonyl, di-(C₁-C₆)-alkylaminothiocarbonyl,(C₃-C₆)-trialkylsilyl, (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino,(C₃-C₆)-cycloalkylamino, aminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,di-(C₁-C₆)-alkylaminosulfonyl, sulfonylamino,(C₁-C₆)-alkylsulfonylamino, di-(C₁-C₆)-alkylsulfonylamino, a phenyl ringor a 3- to 6-membered aromatic, partially saturated or saturatedheterocycle, where the phenyl ring or heterocycle may in each caseoptionally be mono- or polysubstituted by identical or differentsubstituents, and where the substituents independently of one anothermay be selected from the group consisting of (C₁-C₆)-alkyl,(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, (C₃-C₆)-halocycloalkyl,halogen, CN, (C═O)OH, NO₂, OH, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl,(C₁-C₄)-haloalkylsulfonyl, aminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,di-(C₁-C₆)-alkylaminosulfonyl, (C₁-C₆)-alkylcarbonyl,(C₁-C₆)-alkoxycarbonyl, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₄)-alkylaminocarbonyl, tri-(C₁-C₂)-alkylsilyl, or R⁸ representsa 3- to 6-membered aromatic, partially saturated or saturatedheterocycle which is attached via a nitrogen atom and where theheteroatoms are selected from the group consisting of N, S, O, where ineach case at least one carbonyl group may be present and/or theheterocycle may in each case optionally be mono- or polysubstituted byidentical or different substituents, where the substituentsindependently of one another may be selected from the group consistingof (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-halocycloalkyl, halogen, CN, (C═O)OH, NO₂, OH, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,(C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl,(C₁-C₄)-haloalkylsulfonyl, aminosulfonyl, (C₁-C₆)-alkylaminosulfonyl,di-(C₁-C₆)-alkylaminosulfonyl, amino, (C₁-C₄)-alkylamino,di-(C₁-C₄)-alkylamino, (C₃-C₆)-cycloalkylamino, (C₁-C₆)-alkylcarbonyl,(C₁-C₆)-alkoxycarbonyl, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₄)-alkylaminocarbonyl, tri-(C₁-C₂)-alkylsilyl, SF₅, n represents0, 1 or
 2. 2. The compound of formula (I) according to claim 1, whereinA¹ represents nitrogen, ═N⁺(O⁻)— or ═C(R⁴)—, A² represents —N(R⁵)—,oxygen or sulfur, A³ represents oxygen or sulfur, R¹ represents(C₁-C₄)-alkyl, (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-cyanoalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,(C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyloxy-(C₁-C₄)-alkyl,(C₂-C₄)-haloalkynyl, (C₂-C₄)-cyanoalkynyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino,(C₃-C₆)-cycloalkylamino, (C₁-C₄)-alkylcarbonylamino,(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkylthio-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkylsulfinyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkylcarbonyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulfonylamino, orrepresents (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyl,(C₂-C₄)-alkynyl, (C₃-C₆)-cycloalkyl, each of which is optionally mono-or disubstituted by identical or different substituents from the groupconsisting of aryl, hetaryl and heterocyclyl, where aryl, hetaryl andheterocyclyl may each optionally be mono- or disubstituted by identicalor different substituents from the group consisting of halogen, cyano,carbamoyl, aminosulfonyl, (C₁-C₄)-alkyl, (C₃-C₄)-cycloalkyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-alkylsulfimino, or R¹ represents aryl or hetaryl, each of whichis optionally mono- or disubstituted by identical or differentsubstituents from the group consisting of halogen, cyano, carbamoyl,(C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,(C₁-C₄)-alkylsulfonyl, (C₁-C₄)-alkylsulfimino, (C₁-C₄)-alkylsulfoximino,(C₁-C₄)-alkylcarbonyl, and (C₃-C₄)-trialkylsilyl, or R¹ representsheterocyclyl, which is optionally mono- or disubstituted by identical ordifferent substituents from the group consisting of halogen, cyano,carbamoyl, (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-alkylsulfimino,(C₁-C₄)-alkylsulfoximino, (C₁-C₄)-alkylcarbonyl, (C₃-C₄)-trialkylsilyl,(═O) and (═O)₂, R², R³, R⁴ and R⁶ independently of one another representhydrogen, cyano, halogen, nitro, acetyl, hydroxy, amino, SCN,tri-(C₁-C₄)-alkylsilyl, (C₃-C₆)-cycloalkyl,(C₃-C₆)-cycloalkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl,halo-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl,(C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl, (C₂-C₄)-cyanoalkynyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-cyanoalkoxy,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylhydroxyimino,(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkyl-(C₁-C₄)-alkoxyimino,(C₁-C₄)-haloalkyl-(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio,(C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl,(C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfonyloxy, (C₁-C₄)-alkylcarbonyl,(C₁-C₄)-haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)-alkylaminocarbonyl,di-(C₁-C₄)-alkyl-aminocarbonyl, (C₁-C₄)-alkylsulfonylamino,(C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, aminosulfonyl,(C₁-C₄)-alkylaminosulfonyl, di-(C₁-C₄)-alkylaminosulfonyl,aminothiocarbonyl, NHCO—(C₁-C₄)-alkyl ((C₁-C₄)-alkylcarbonylamino), SF₅or represent phenyl or hetaryl, each of which is optionally mono- ordisubstituted by identical or different substituents, where in the caseof hetaryl at least one carbonyl group may optionally be present and/orwhere optional substituents are in each case as follows: cyano, halogen,nitro, acetyl, amino, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,(C₁-C₄)-cyanoalkyl, (C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₂-C₄)-alkenyl, (C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl,(C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl, (C₂-C₄)-cyanoalkynyl,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-cyanoalkoxy,(C₁-C₄)-alkoxy-(C₁-C₄)-alkoxy, (C₁-C₄)-alkylhydroxyimino,(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkyl-(C₁-C₄)-alkoxyimino,(C₁-C₄)-haloalkyl-(C₁-C₄)-alkoxyimino, (C₁-C₄)-alkylthio,(C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl,(C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfonyloxy, (C₁-C₄)-alkylcarbonyl,(C₁-C₄)-haloalkylcarbonyl, aminocarbonyl, (C₁-C₄)-alkylaminocarbonyl,di-(C₁-C₄)-alkylpaminocarbonyl, (C₁-C₄)-alkylsulfonylamino,(C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, aminosulfonyl,(C₁-C₄)-alkylaminosulfonyl, di-(C₁-C₄)-alkylaminosulfonyl, R⁵ represents(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-cyanoalkyl,(C₁-C₄)-hydroxyalkyl, (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkoxy-(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-alkenyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkenyloxy-(C₁-C₄)-alkyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-cyanoalkenyl, (C₂-C₄)-alkynyl,(C₂-C₄)-alkynyloxy-(C₁-C₄)-alkyl, (C₂-C₄)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₃-C₆)cycloalkyl,(C₁-C₄)-alkyl-(C₃-C₆)cycloalkyl, halo-(C₃-C₆)-cycloalkyl,(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl, (C₁-C₄)-haloalkylthio-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkylsulfinyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl,(C₁-C₄)-haloalkylsulfonyl-(C₁-C₄)-alkyl,(C₁-C₄)-alkoxy-(C₁-C₄)-alkylthio-(C₁-C₄)-alkyl or(C₁-C₄)-alkylcarbonyl-(C₁-C₄)-alkyl, R⁷ represents hydrogen orrepresents (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl,(C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₁₂)-cycloalkyl-(C₁-C₆)-alkylor (C₄-C₁₂)-bicycloalkyl, each of which is optionally mono- orpolysubstituted by identical or different substituents, where thesubstituents independently of one another may be selected from the groupconsisting of halogen, cyano, (C₁-C₆)-alkyl, (C₁-C₄)-haloalkyl,(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₂-C₆)-alkoxycarbonyl, (C₂-C₆)-alkylcarbonyl, a phenyl ring or a 3- or6-membered aromatic, partially saturated or saturated heterocycle, wherethe phenyl ring or heterocycle may in each case optionally be mono- orpolysubstituted by identical or different substituents, and where thesubstituents independently of one another may be selected from the groupconsisting of (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-halocycloalkyl, halogen, cyano,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,(C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl,(C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl, aminocarbonyl,(C₁-C₆-alkyl)aminocarbonyl, di-(C₁-C₄-alkyl)aminocarbonyl, R⁸ representsamino or (C₁-C₆)-alkylamino, di-(C₁-C₄)-alkylamino,(C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₃-C₁₂)-cycloalkylamino,(C₃-C₁₂)-cycloalkyl-(C₁-C₆)-alkylamino, (C₄-C₁₂)-bicycloalkylamino orhydrazino, each of which is optionally mono- or polysubstituted byidentical or different substituents, where the substituentsindependently of one another may be selected from the group consistingof halogen, cyano, amino, nitro, hydroxy, (C═O)OH, (C₁-C₆)-alkyl,(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylsulfinyl,(C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-haloalkylsulfonyl, (C₂-C₆)-alkoxycarbonyl,(C₂-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₆)-alkylcarbonylamino, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₆)-alkylaminocarbonyl, (C₁-C₄)-alkylamino,di-(C₁-C₄)-alkylamino, (C₃-C₆)-cycloalkylamino, aminosulfonyl,(C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,sulfonylamino, (C₁-C₆)-alkylsulfonylamino,di-(C₁-C₆)-alkylsulfonylamino, a phenyl ring or a 3- to 6-memberedaromatic, partially saturated or saturated heterocycle, where the phenylring or heterocycle may in each case optionally be mono- orpolysubstituted by identical or different substituents, and where thesubstituents independently of one another may be selected from the groupconsisting of (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl,(C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl,(C₂-C₆)-haloalkynyl, (C₃-C₆)-halocycloalkyl, halogen, cyano, (C═O)OH,NO₂, OH, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,(C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl, aminosulfonyl,(C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl, aminocarbonyl,(C₁-C₆)-alkylaminocarbonyl, di-(C₁-C₄)-alkylaminocarbonyl, or R⁸represents a 3- to 6-membered aromatic, partially saturated or saturatedheterocycle which is attached via a nitrogen atom and where theheteroatoms are selected from the group consisting of N, S, O, where ineach case at least one carbonyl group may be present and/or theheterocycle may in each case optionally be mono- or polysubstituted byidentical or different substituents, where the substituentsindependently of one another may be selected from the group consistingof (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl,(C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl,(C₃-C₆)-halocycloalkyl, halogen, cyano, (C═O)OH, NO₂, OH,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,(C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl, aminosulfonyl,(C₁-C₆)-alkylaminosulfonyl, di-(C₁-C₆)-alkylaminosulfonyl, amino,(C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, (C₃-C₆)-cycloalkylamino,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkoxycarbonyl, aminocarbonyl,(C₁-C₆)-alkylaminocarbony or di-(C₁-C₄)-alkylaminocarbonyl, n represents0, 1 or
 2. 3. The compound of formula (I) according to claim 1 whereinA¹ represents nitrogen or ═C(R⁴)—, A² represents —N(R⁵)— or oxygen, A³represents oxygen or sulfur, R¹ represents (C₁-C₄)-alkyl,(C₁-C₄)-hydroxyalkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,(C₂-C₄)-haloalkenyl, (C₂-C₄)-alkynyl, (C₂-C₄)-haloalkynyl,(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkylthio-(C₁-C₄)-alkyl,(C₁-C₄)-alkylsulfinyl-(C₁-C₄)-alkyl or(C₁-C₄)-alkylsulfonyl-(C₁-C₄)-alkyl, R² represents hydrogen, cyano,halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl or(C₁-C₄)-haloalkylsulfonyl, R³ represents hydrogen, halogen,(C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,(C₁-C₄)-haloalkylsulfinyl or (C₁-C₄)-haloalkylsulfonyl, R⁴ representshydrogen, halogen, cyano or (C₁-C₄)-alkyl, R⁵ represents (C₁-C₄)-alkylor (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, R⁶ represents hydrogen, cyano, halogen,(C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-haloalkyl,(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkyl-(C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-haloalkylsulfonyl or (C₁-C₄)-alkylcarbonyl, R⁷ representshydrogen or represents (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl,each of which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of halogen,(C₁-C₂)-haloalkyl, cyano, phenyl and pyridyl, where phenyl and pyridylmay each optionally be mono- or disubstituted by identical or differentsubstituents from the group consisting of (C₁-C₄)-alkyl, halogen andcyano, R⁸ represents amino or (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino,(C₂-C₆)-alkenylamino, (C₂-C₄)-alkynylamino, (C₃-C₆)-cycloalkylamino orhydrazino, each of which is optionally mono- or polysubstituted byidentical or different substituents, where the substituentsindependently of one another may be selected from the group consistingof halogen, cyano, (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-alkylsulfonyl,(C₁-C₄)-haloalkylsulfonyl, (C₁-C₄)-alkoxycarbonyl,(C₁-C₄)-alkylcarbonyl, (C₁-C₆)-haloalkylcarbonyl,(C₁-C₄)-alkylcarbonylamino, aminocarbonyl, (C₁-C₆)-alkylaminocarbonyl,di-(C₁-C₆)-alkylaminocarbonyl, a phenyl ring or a 3- to 6-memberedaromatic, partially saturated or saturated heterocycle, where the phenylring or heterocycle may in each case optionally be mono- orpolysubstituted by identical or different substituents, and where thesubstituents independently of one another may be selected from the groupconsisting of (C₁-C₄)-alkyl, (C₃-C₆)-cycloalkyl, (C₁-C₄)-haloalkyl,halogen, cyano, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylsulfinyl, (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio,(C₁-C₄)-haloalkylsulfinyl, (C₁-C₄)-haloalkylsulfonyl, or R⁸ represents a3- to 6-membered aromatic, partially saturated or saturated heterocyclewhich is attached via a nitrogen atom and where the heteroatoms areselected from the group consisting of N, S, O, where in each case atleast one carbonyl group may be present and/or the heterocycle may ineach case optionally be mono- or polysubstituted by identical ordifferent substituents, where the substituents independently of oneanother may be selected from the group consisting of (C₁-C₄)-alkyl,(C₃-C₆)-cycloalkyl, (C₁-C₆)-haloalkyl, halogen, cyano, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulfinyl,(C₁-C₄)-alkylsulfonyl, (C₁-C₄)-haloalkylthio, (C₁-C₄)-haloalkylsulfinyl,(C₁-C₄)-haloalkylsulfonyl, n represents 0, 1 or
 2. 4. The compound offormula (I) according to claim 1, wherein A¹ represents nitrogen or═C(R⁴)—, A² represents —N(R⁵)— or oxygen, A³ represents oxygen orsulfur, R¹ represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl,n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl,trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,tetrafluoroethyl or pentafluoroethyl, R² represents hydrogen, methyl,ethyl, fluorine, chlorine, bromine, cyano, fluoromethyl, difluoromethyl,trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl,tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy,difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio,trifluoromethylsulfinyl or trifluoromethylsulfonyl, R³ representsfluorine, chlorine, fluoromethyl, difluoromethyl, trifluoromethyl,fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl,pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy,dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl ortrifluoromethylsulfonyl, R⁴ represents hydrogen, fluorine, chlorine,bromine or cyano, R⁵ represents methyl, ethyl, isopropyl, methoxymethylor methoxyethyl, R⁶ represents hydrogen, R⁷ represents hydrogen, methyl,ethyl, isopropyl, tert-butyl, methoxymethyl or methoxyethyl, R⁸represents amino or represents methylamino, dimethylamino, ethylamino,isopropylamino, diethylamino, methylethylamino, propylamino,methylpropylamino, ethylpropylamino, methoxyethylamino, cyanoethylamino,methylthioethylamino, methylsulfinylethylamino,methylsulfonylethylamino, cyclopropylamino, cyclobutylamino,methylcyclopropylamino, methylcyclobutylamino, methylhydrazino,dimethylhydrazino, trimethylhydrazino or phenylhydrazino, or R⁸represents aziridinyl, azetidinyl, pyrrolidinyl, pyrazolidinyl,imidazolidinyl, thiazolidinyl, oxazolidinyl, piperidinyl, piperazinyl,morpholinyl, thiomorpholinyl, pyrrolidonyl, imidazolidonyl,triazolinonyl, tetrazolinonyl, piperidonyl, pyrrolyl, pyrazolyl,triazolyl, imidazolyl or oxazolyl, attached via a nitrogen atom, in eachcase optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of methyl, ethyl,trifluoromethyl, fluorine, chlorine, bromine and cyano, n represents 0,1 or
 2. 5. The compound of formula (I) according to claim 1, wherein A¹represents nitrogen, A² represents —N(R⁵)—, A³ represents oxygen, R¹represents ethyl, R² represents hydrogen, methyl or trifluoromethyl, R³represents trifluoromethyl, pentafluoroethyl, trifluoromethylthio,trifluoromethylsulfinyl or trifluoromethylsulfonyl, R⁵ representsmethyl, R⁶ represents hydrogen, R⁷ represents hydrogen or methyl, R⁸represents amino, methylamino, dimethylamino, ethylamino,isopropylamino, cyclopropylamino, methoxyethylamino, cyanoethylamino,methylthioethylamino, methylsulfinylethylamino ormethylsulfonylethylamino, or R⁸ represents pyrrolidinyl, attached via anitrogen atom, or represents pyrazolyl, attached via a nitrogen atom andoptionally monosubstituted by bromine, n represents 0, 1 or
 2. 6. Thecompound of formula (I) according to claim 1, wherein A¹ representsnitrogen, A² represents —N—(R⁵)—, A³ represents oxygen, R¹ representsethyl, R² represents hydrogen or methyl, R³ represents trifluoromethyl,R⁵ represents methyl, R⁶ represents hydrogen, R⁷ represents hydrogen ormethyl, R⁸ represents methylamino (—NHCH₃), ethylamino (—NHCH₂CH₃),isopropylamino (—NHiC₃H₇), methoxyethylamino (—NHCH₂CH₂OCH₃,cyanoethylamino (—NHCH₂CH₂CN), methylthioethylamino (—NHCH₂CH₂SCH₃),methylsulfinylethylamino (—NHCH₂CH₂SOCH₃), methylsulfonylethylamino(—NHCH₂CH₂SO₂CH₃) or dimethylamino (—N(CH₃)₂), or R⁸ representspyrrolidinyl, attached via a nitrogen atom, or represents pyrazolyl,attached via a nitrogen atom and optionally monosubstituted by bromine,n represents
 2. 7. The compound of formula (I) according to claim 1,wherein A¹ represents nitrogen, A² represents —N—(R⁵)—, A³ representsoxygen, R¹ represents ethyl, R² represents hydrogen or methyl, R³represents trifluoromethyl, R⁵ represents methyl, R⁶ representshydrogen, R⁷ represents hydrogen or methyl, R⁸ represents methylamino(—NHCH₃), ethylamino (—NHCH₂CH₃), isopropylamino (—NHiC₃H₇),methoxyethylamino (—NHCH₂CH₂OCH₃), cyanoethylamino (—NHCH₂CH₂CN),methylthioethylamino (—NHCH₂CH₂SCH₃), methylsulfinylethylamino(—NHCH₂CH₂SOCH₃), methylsulfonylethylamino (—NHCH₂CH₂SO₂CH₃) ordimethylamino (—N(CH₃)₂), or R⁸ represents pyrrolidinyl, attached via anitrogen atom, of the formula below:

or represents pyrazolyl, attached via a nitrogen atom andmonosubstituted by bromine, of the formula:

n represents
 2. 8. Agrochemical formulation comprising the compound offormula (I) according to claim 1 and also one or more extenders and/orsurfactants.
 9. Agrochemical formulation according to claim 8, furthercomprising an additional agrochemically active compound.
 10. A methodfor controlling one or more arthropod pests, comprising applying thecompound of formula (I) according to claim 1 to the arthropod pestsand/or a habitat thereof.
 11. A product comprising the compound offormula (I) according to claim 1 for controlling one or more arthropodpests.
 12. A method for controlling one or more arthropod pests,comprising applying the agrochemical formulation according to claim 8 tothe arthropod pests and/or a habitat thereof.
 13. A product comprisingthe agrochemical formulation according to claim 8 for controlling one ormore arthropod pests.